Abstract
AbstractThis review article is an attempt to sketch the important developments in organic synthesis during the past 25 years, and to project them into the future.—The primary motivations that once induced chemists to undertake natural product syntheses no longer exist. Instead of target structures themselves, molecular function and activity now occupy center stage. Thus, inhibitors with an affinity for all the important natural enzymes and receptors have moved to the fore as potential synthetic targets.—New syntheticmethodsare most likely to be encountered in the fields of biological and organometallic chemistry. Enzymes, whole organisms, and cell cultures for enan‐tioselective synthesis of specific substances have already been incorporated into the synthetic arsenals of both research laboratories and industry. In addition, designing appropriate analogues to transition states and intermediates should soon make it possible, with the aid of the mammalian immune system and gene technology, to prepare catalytically active monoclonal antibodies for almost any reaction; perhaps, more important, such processes will increasingly come to be applied on an industrial scale.‐The discovery of truly new reactions is likely to be limited to the realm of transition‐metal organic chemistry, which will almost certainly provide us with additional “miracle reagents” in the years to come. As regards main group elements (“organoelemental chemistry”), we can surely anticipate further stepwise improvements in experimental procedures and the broader application of special techniques, leading to undreamed of efficiency and selectivity with respect to known procedures. The primary center of attention for all synthetic methods will continue to shift toward catalytic and enantioselective variants; indeed, it will not be long before such modifications will be available with every standard reaction for converting achiral educts into chiral products. Analysis, spectroscopy, structure determination, theory, and electronic data processing have all become indispensable in organic synthesis. Only with the aid of these “tools” will the methods of organic chemistry permit selective syntheses of ever larger and more complex systems on both the molecular and supramolecular levels.—Examples have been introduced throughout this discourse to illustrate its many themes, and a very comprehensive bibliography should help the interested reader become more familiar with important keywords and authors.[The list of references is also available upon request in the form of a Microsoft Word© file on diskette.]—This article will have served its intended purpose if it changes the minds of some of those who claim organic chemistry is amature science, and if it causes students to discover the vitality and forcefulness with which organic synthesis is meeting new challenges and attempting to fulfill old dreams.Er zeigt uns so in seinem wissenschaftlichen Leben, daß die Chemie nicht von einer Theorie, nicht von einer Methode aus zu erschöpfen ist, und daß Erkenntnis und Nutzen in ihr untrennbar verwoben sind.“He showed us through his scientific life that chemistry cannot be exploited fully with the aid of asingletheory or asinglemethodology, and that it is a field in which knowledge and application are inextricably linked.” G. Bugge:Das Buch der großen Chemiker, Vol. 2, 4th reprint, Verlag Chemie, Weinheim 1974.R. Koch, writing about Louis Pasteur
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10.5059/yukigoseikyokaishi.47.27
10.1002/nadc.19900380112
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10.5059/yukigoseikyokaishi.45.664
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(j) “New Catalytic Reactions of the Hydrolytic Enzymes in Fluorine Chemistry”:T.Kilazume T.Yamazaki 45(1987)888–897;
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10.5059/yukigoseikyokaishi.45.888
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{'key': 'e_1_2_1_92_13', 'first-page': '97', 'volume': '10', 'author': 'Imperiali B.', 'year': '1988', 'journal-title': 'Adv. Biotechnol. Processes'}
/ Adv. Biotechnol. Processes by Imperiali B. (1988)- As an outsider one has the impression that specialists take it for granted that reactions of “normal” compoundswon'twork with fluorine derivatives; if they do succeed the astonishing news warrants immediate publication! A few personal experiences would suggest that one should be prepared for anything with even the simplest reactions—a thrilling prospect; see [94–97] (cf. also Chapter 4. “Aliphatic Fluoronitro Com‐pounds” in [105a]).
10.1002/hlca.19840670721
10.1002/hlca.19850680829
10.1002/ange.19860980121
10.1002/anie.198600981
- “Fluorierte Nitro‐ und Aminoalkohole”:D.Seebach A. K.Beck DOS 3 540 332 (1987) Bayer AG;
{'key': 'e_1_2_1_96_3', 'first-page': '115 246e', 'volume': '107', 'year': '1987', 'journal-title': 'Chem. Abstr.'}
/ Chem. Abstr. (1987)- “Verfahren zur Herstellung von fluorierten Nitroalkylverbindungen”:D.Seebach A. K.Beck DOS 3 808 276 (1988).Bayer AG;
{'key': 'e_1_2_1_96_5', 'first-page': '98013k', 'volume': '112', 'year': '1990', 'journal-title': 'Chem. Abstr.'}
/ Chem. Abstr. (1990)- “Synthesis of Fluorinated Nitro‐ and Aminoalcohols”:B.Baasner M. J.Negele A. K.Beck D.Seebach 12th Int. Symp. Fluorine Chem.7–12 Aug. 1988 Santa Cruz CA (USA) Abstr. 331.
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/ Chimia by Ács M. (1990)10.2533/chimia.1990.291
/ Chimia by Beck A. K. (1990)10.1021/ja01105a527
10.1016/S0083-6729(08)60320-9
{'key': 'e_1_2_1_98_4', 'first-page': '402', 'volume-title': 'Arzneimittel', 'author': 'Ehrhart G.', 'year': '1972'}
/ Arzneimittel by Ehrhart G. (1972)10.1021/jm00149a001
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{'key': 'e_1_2_1_102_2', 'first-page': 'S1', 'volume': '1987', 'author': 'Allen F. H.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 2'}
/ J. Chem. Soc. Perkin Trans. 2 by Allen F. H.{'key': 'e_1_2_1_102_3', 'first-page': '81', 'volume': '1989', 'author': 'Orpen A. G.', 'journal-title': 'J. Chem. Soc. Dalton Trans.'}
/ J. Chem. Soc. Dalton Trans. by Orpen A. G.- see also [107b].
10.1021/ar00095a005
{'key': 'e_1_2_1_104_2', 'volume-title': 'Nitro Compounds—Recent Advances in Synthesis and Chemistry', 'author': 'Feuer H.', 'year': '1990'}
/ Nitro Compounds—Recent Advances in Synthesis and Chemistry by Feuer H. (1990){'key': 'e_1_2_1_104_3', 'volume-title': 'Nitration—Methods and Mechanisms', 'author': 'Olah G. A.', 'year': '1989'}
/ Nitration—Methods and Mechanisms by Olah G. A. (1989){'key': 'e_1_2_1_104_4', 'volume-title': 'Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis—Novel Strategies in Synthesis', 'author': 'Torssell K. B. G.', 'year': '1988'}
/ Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis—Novel Strategies in Synthesis by Torssell K. B. G. (1988)-
(d) “Functionalized Nitroalkanes are Useful Reagents for Alkyl Anion Synrtheses”:G.Rosini R.Ballini Synthesis1988 833–847.
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{'key': 'e_1_2_1_106_2', 'first-page': '169', 'volume': '10', 'author': 'Tacke R.', 'year': '1987', 'journal-title': 'Main Group Met. Chem.'}
/ Main Group Met. Chem. by Tacke R. (1987)10.1002/0470025107.ch1
10.1021/cr00097a014
10.1351/pac198860010099
{'key': 'e_1_2_1_107_3', 'first-page': '831', 'volume-title': 'Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.)', 'author': 'Hosomi A.', 'year': '1989'}
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10.1021/ja00192a041
10.1002/nadc.19890370110
- see also the references in Schemes 15 and 16 and in Table 3;
{'key': 'e_1_2_1_107_8', 'volume-title': 'Molecular Structure of Organosilicon Compounds.', 'author': 'Lukevics E.', 'year': '1989'}
/ Molecular Structure of Organosilicon Compounds. by Lukevics E. (1989)10.1021/ar50120a003
{'key': 'e_1_2_1_109_2', 'volume-title': 'Silicon in Organic Synthesis', 'author': 'Colvin E. W.', 'year': '1981'}
/ Silicon in Organic Synthesis by Colvin E. W. (1981){'key': 'e_1_2_1_109_3', 'first-page': '539', 'volume-title': 'The Chemistry of the Metal–Carbon Bond', 'author': 'Colvin E. W.', 'year': '1987'}
/ The Chemistry of the Metal–Carbon Bond by Colvin E. W. (1987){'key': 'e_1_2_1_109_4', 'volume-title': 'Silicon Reagents in Organic Synthesis', 'author': 'Colvin E. W.', 'year': '1988'}
/ Silicon Reagents in Organic Synthesis by Colvin E. W. (1988)10.1007/978-3-642-68661-0
{'key': 'e_1_2_1_109_6', 'volume-title': 'Silicon Chemistry', 'author': 'Corey J. Y.', 'year': '1988'}
/ Silicon Chemistry by Corey J. Y. (1988)10.1002/0470025107
10.1021/ja01063a015
{'key': 'e_1_2_1_110_3', 'first-page': '3809', 'volume': '1966', 'author': 'Pracejus H.', 'journal-title': 'Tetrahedron Lett.'}
/ Tetrahedron Lett. by Pracejus H.10.1021/ja00812a047
{'key': 'e_1_2_1_111_2', 'volume-title': 'Reaction Rates of Isotopic Molecules', 'author': 'Melander L.', 'year': '1980'}
/ Reaction Rates of Isotopic Molecules by Melander L. (1980)10.1126/science.3787261
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- Review articles on this topic: (a) “Enzymes and Abzymes”:S. J.Benkovic Proc. Robert A. Welch Found. Conf. Chem. Res. 31: esign of Enzymes and Enzyme Models 2–4 Nov. 1987 Houston TX 1987 pp. 113–125;
10.1002/ange.19891011005
10.1002/anie.198912833
10.1021/ar00164a005
{'key': 'e_1_2_1_114_6', 'first-page': '1', 'volume': '3', 'author': 'Lerner R. A.', 'year': '1990', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Lerner R. A. (1990)10.1038/scientificamerican0388-58
{'issue': '5', 'key': 'e_1_2_1_114_8', 'first-page': '78', 'volume': '1988', 'journal-title': 'Spektrum Wiss'}
/ Spektrum Wiss10.1021/ja00197a078
10.1021/ja00222a060
10.1073/pnas.85.14.4953
10.1021/ja00304a064
10.1021/ja00208a037
10.1126/science.2531466
10.1002/ange.19850971005
10.1002/anie.198508101
10.1002/ange.19850971006
10.1002/anie.198508161
10.1002/ange.19850971007
10.1002/anie.198508271
10.1126/science.2717936
10.1126/science.2922606
10.1126/science.3616626
10.1021/ja00207a022
10.1002/ange.19881000925
10.1002/anie.198811721
{'key': 'e_1_2_1_125_2', 'first-page': '354', 'volume': '1986', 'author': 'Klibanov A. M.', 'journal-title': 'CHEMTECH'}
/ CHEMTECH by Klibanov A. M.10.1021/ja00208a044
10.1021/ar00172a004
{'key': 'e_1_2_1_126_2', 'first-page': '1', 'volume': '37', 'author': 'Ohno M.', 'year': '1989', 'journal-title': 'Org. React. (N. Y.)'}
/ Org. React. (N. Y.) by Ohno M. (1989)10.1002/hlca.19880710102
10.1039/cs9901900001
10.1016/0003-2697(85)90094-6
10.1021/bi00369a003
10.1126/science.2649980
{'key': 'e_1_2_1_129_3', 'first-page': '302', 'volume': '2', 'author': 'Hopkins M. H.', 'year': '1989', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Hopkins M. H. (1989)10.1021/ja00202a052
- The predictions expressed here will come to pass in Germany only if “the thorny path to gene technology for the pharmaceutical industry in the Federal Republic” (headline in theNeue Zürcher Zeitungfor 20 March 1990 p. 39) is in the end traversed successfully. A treatment of the problematics by one who should know: “Biotechnologie ausder Sicht der Industrie”: K. H. Büchel in Kernforschungsanlage Jülich GmbH (Ed.):Festvortrag anläßlich der Einweihung des Biotechnikums der Kern‐forschungsanlage Eilich GmbH. 15. April 1988. Jülich (ISBN 3–89336–004–2).
10.1002/ange.19881000405
10.1002/anie.198804601
{'key': 'e_1_2_1_133_2', 'volume-title': 'The Practice of Enantiomer Separation by Capillary Gas Chromatography', 'author': 'König W. A.', 'year': '1987'}
/ The Practice of Enantiomer Separation by Capillary Gas Chromatography by König W. A. (1987)10.1002/nadc.19890370506
{'key': 'e_1_2_1_133_4', 'first-page': '367', 'volume': '112', 'author': 'Martens J.', 'year': '1988', 'journal-title': 'Chem.‐Ztg.'}
/ Chem.‐Ztg. by Martens J. (1988){'key': 'e_1_2_1_133_5', 'first-page': '6', 'volume': '3', 'author': 'Günther K.', 'year': '1986', 'journal-title': 'GIT Suppl.'}
/ GIT Suppl. by Günther K. (1986)10.1021/cr00092a006
{'key': 'e_1_2_1_133_7', 'first-page': '104', 'volume': '3', 'author': 'Kinkel J. N.', 'year': '1989', 'journal-title': 'GIT Suppl.'}
/ GIT Suppl. by Kinkel J. N. (1989)10.1016/S0021-9673(00)80205-8
{'key': 'e_1_2_1_134_2', 'volume-title': 'Analytical Methods.', 'author': 'Morrison J. D.', 'year': '1983'}
/ Analytical Methods. by Morrison J. D. (1983){'issue': '1', 'key': 'e_1_2_1_134_3', 'first-page': '54', 'volume': '1985', 'author': 'Schurig V.', 'journal-title': 'Kontakte (Darmstadt)'}
/ Kontakte (Darmstadt) by Schurig V.{'issue': '2', 'key': 'e_1_2_1_134_4', 'first-page': '22', 'volume': '1985', 'journal-title': 'Kontakte (Darmstadt)'}
/ Kontakte (Darmstadt){'issue': '1', 'key': 'e_1_2_1_134_5', 'first-page': '3', 'volume': '1986', 'journal-title': 'Kontakte (Darmstadt)'}
/ Kontakte (Darmstadt){'key': 'e_1_2_1_134_6', 'volume-title': 'Chromatographic Enantioseparation: Methods and Applications', 'author': 'Allenmark G.', 'year': '1988'}
/ Chromatographic Enantioseparation: Methods and Applications by Allenmark G. (1988)10.1515/znb-1983-1019
/ Z. Naturfarsch. B. by Bayer E. (1983)10.1002/ange.19891010626
10.1002/anie.198907361
10.1002/hlca.19880710541
10.1016/S0378-4347(00)84480-1
10.1021/ac00201a010
- I wish to thank ProfessorKarger Barnett Institute and Department of Chemistry Northeastern University Boston MA for placing at my disposal the HPCE spectra;
- “Kapillarelektrophorese—ein Durchbruch in der Separationstechnik”:V. P.Burolla S. L.Pentoney R.Zare Beckman Rep.Issue 70 May 1990 pp. 2–3 (with 31 references);
10.1002/nadc.19900380514
{'key': 'e_1_2_1_139_2', 'first-page': '320', 'volume': '43', 'author': 'Widmer H. M.', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia by Widmer H. M. (1989){'key': 'e_1_2_1_140_2', 'first-page': '357', 'volume': '43', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia (1989)10.2533/chimia.1990.22
/ Chimia (1990){'key': 'e_1_2_1_141_2', 'volume-title': 'Principles of nuclear magnetic resonance in one and two dimensions', 'author': 'Ernst R. R.', 'year': '1987'}
/ Principles of nuclear magnetic resonance in one and two dimensions by Ernst R. R. (1987){'key': 'e_1_2_1_141_3', 'first-page': '323', 'volume': '41', 'author': 'Ernst R. R.', 'year': '1987', 'journal-title': 'Chimia'}
/ Chimia by Ernst R. R. (1987){'key': 'e_1_2_1_141_4', 'volume-title': 'Two Dimensional NMR Spectroscopy', 'author': 'Croasmun W. R.', 'year': '1987'}
/ Two Dimensional NMR Spectroscopy by Croasmun W. R. (1987)10.1002/ange.19881000407
10.1002/anie.198804901
10.1002/ange.19901020409
10.1002/anie.199003741
10.1016/0022-2364(87)90027-8
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10.1038/332374a0
10.1016/0006-291X(80)90695-6
10.1016/0022-2836(82)90009-2
10.1021/ja00202a065
10.1002/mrc.1270170114
- Z.Brich H.‐R.Loosli previously unpublished experiments. Sandoz AG Basel 1982. I wish to thank Dr.Brichfor providing the spectra along with permission to reproduce one of them here.
10.1021/jo00197a027
10.1021/ja00293a001
10.1021/ja00293a002
10.1021/ja00240a047
10.1021/jo00292a030
10.1002/ange.19820940705
10.1002/anie.198205121
10.1051/epn/19861701011
10.1021/ar00157a006
10.1016/0092-8674(89)90040-8
10.1007/978-3-642-74692-5
10.1002/ange.19881001207
10.1002/anie.198816551
10.1002/ange.19881001107
10.1002/anie.198814681
10.1002/ange.19901020104
10.1002/anie.199000013
{'key': 'e_1_2_1_154_2', 'volume-title': 'Field Desorption Mass Spectrometry', 'author': 'Prokai L.', 'year': '1990'}
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10.1002/ange.19881000404
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10.1021/ma00158a053
10.2533/chimia.1990.112
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- Theophrastus Bombastus Paracelsus von Hohenheim (1493–1541): “Was ist das nit gifft is to alle ding sind gifft (und nichts ohn gifft). Aliein die dosis macht das ein ding kein gifft ist” [Dosis facit venenum 1537;
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10.1038/329178a0
- “Structural Studies on Macromolecules and Viruses with Laue Diffraction”: J. Hajdu Lecture in the Physical‐Chemical Colloquium of the ETH Zürich 28 March 1990. I wish to thank Dr.Hajduand ProfessorPhillips(Oxford) for stimulating discussions. I am grateful to Dr.Hajdufor the Laue diffraction pattern shown in Fig. 5 and the data in the caption.
10.1002/ange.19881000109
10.1002/anie.198800791
10.1002/ange.19891010704
10.1002/anie.198908481
{'key': 'e_1_2_1_166_4', 'first-page': '872', 'volume': '101', 'author': 'Deisenhofer J.', 'year': '1989', 'journal-title': 'Rhodopseudomonas viridis'}
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(c)E.Hahn T.Maetzke D. A.Plattner D.Seebach Chem. Ber.123(1990) in press.
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- E. HahnundS. Rupprecht(Institut für Anorganische und Analytische Chemie der Technischen Universitat Berlin) recently determined the structure of [(LiCl)2· 4THF] which begins to lose solvent and decompose above −60° C. Single crystals can only be isolated directly from the mother liquor.
10.1002/ange.19860980307
10.1002/anie.198602761
10.1002/ange.19870990620
10.1002/anie.198705601
10.1021/ja00208a017
10.1002/ange.19881001206
10.1002/anie.198816241
10.1002/ange.19891010306
10.1002/anie.198902771
10.1016/0022-328X(85)87352-6
10.1016/S0040-4020(01)91914-3
10.1002/ange.19840960321
10.1002/anie.198402481
{'key': 'e_1_2_1_175_5', 'first-page': '233', 'volume': '39', 'author': 'Seebach D.', 'year': '1985', 'journal-title': 'Chimia'}
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T.Maetzke C. P.Hidber D.Seebach J. Am. Chem. Soc.112(1990) in press;
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T.Maetzke D.Seebach Orgnnometallics9(1990) in press.
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10.1002/anie.197504601
10.1021/ar00089a002
10.1021/ja00244a012
10.1107/S010876818800374X
10.1021/ja00223a012
- For discussions regarding the possible relationship between the packing of carbocation counterions in the crystal and their behavior during solvolyses see [171].
10.1002/ange.19901020307
10.1002/anie.199002561
10.1002/ange.19881000705
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D.Seebach T.Maetzke W.Petter B.Klötzer D. A.Plattner J. Am. Chem. Soc.112(1990) in press.
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10.1002/anie.198912391
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10.1016/0040-4020(80)88015-X
10.1021/ja00531a047
10.1107/S0567740879009249
{'key': 'e_1_2_1_190_2', 'first-page': '589', 'volume': '25', 'author': 'Long D. A.', 'year': '1989', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by Long D. A. (1989)10.1002/ange.19870990705
10.1002/anie.198706061
10.1002/ange.19891010857
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/ Adv. Mater.10.1126/science.2727694
- The equipment manufacturers (i.e. ultimately the commercial aspects) help to determine which methods actually find entry into the daily practice of lhe synthetic chemist and how quickly.
{'key': 'e_1_2_1_194_2', 'volume-title': 'Chemical Information—Information in Chemistry. Pharmacology and Patents', 'author': 'Collier H. R.', 'year': '1989'}
/ Chemical Information—Information in Chemistry. Pharmacology and Patents by Collier H. R. (1989)10.1021/bk-1989-0400
/ Chemical Structure Information Systems—Interfaces, Communication, and Standards by Warr W. A. (1989){'key': 'e_1_2_1_194_4', 'volume-title': 'Computer Aids to Chemistry', 'author': 'Vernin G.', 'year': '1986'}
/ Computer Aids to Chemistry by Vernin G. (1986)- S.Rubenstein Cambridge Scientific Computing Inc. 875 Massachusetts Ave. Suite 41 Cambridge MA 02139;
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/ A Guide for the Perplexed Organic Experimentalist by Zass E. (1990){'key': 'e_1_2_1_196_3', 'volume-title': 'Chemical information: a practical guide to utilization', 'author': 'Wolman Y.', 'year': '1988'}
/ Chemical information: a practical guide to utilization by Wolman Y. (1988){'key': 'e_1_2_1_196_4', 'volume-title': 'Online‐Recherchen für Chemiker', 'author': 'Pichler H. R.', 'year': '1986'}
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{'issue': '5', 'key': 'e_1_2_1_198_2', 'first-page': '43', 'volume': '40', 'author': 'Braun H. W.', 'year': '1988', 'journal-title': 'Chem. Ind. (Düsseldorf)'}
/ Chem. Ind. (Düsseldorf) by Braun H. W. (1988){'key': 'e_1_2_1_199_2', 'first-page': '267', 'volume-title': 'Organic Synthesis, an interdisciplinary challenge', 'author': 'Hanes‐sian S.', 'year': '1985'}
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{'key': 'e_1_2_1_201_2', 'first-page': '38', 'volume': '40', 'author': 'Zass E.', 'year': '1986', 'journal-title': 'Chimia'}
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/ Chem. Br. by Johnson A. P. (1985)- Molecular Design Ltd. 2132 Farallon Drive San Leandro CA 94577; Molecular Design MDA AG Mühlebachweg 9 CH‐4123 Allschwil 2 (Switzerland);
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/ Chem. Mag. (Rijswijk, Neth.) by Liskamp R. M. J.10.1002/jcc.540110405
{'key': 'e_1_2_1_208_2', 'volume': '177', 'author': 'Burkert U.', 'year': '1982', 'journal-title': 'ACS Monogr.'}
/ ACS Monogr. by Burkert U. (1982)- The use of force field methods with the full set of parameters (MacroModel) requires a high‐resolution color graphics terminal (e.g. the Evans–Sutherland Picture System).
{'key': 'e_1_2_1_210_2', 'volume-title': 'Ab Initia Molecular Orbital Theory', 'author': 'Hehre W. J.', 'year': '1986'}
/ Ab Initia Molecular Orbital Theory by Hehre W. J. (1986)- M. R.Peterson R. A.Poirier:Monster‐Gauss Departments of Chemistry University of Toronto Toronto and Memorial University of Newfoundland. St. John's (Canada).
- R. D.Amos J. E.Rice:The Cambridge Analytic Derivatives Package Issue 4.1 L. GB‐Cambridge.
{'key': 'e_1_2_1_213_2', 'first-page': '115', 'volume': '7', 'author': 'Schmidt M. W.', 'year': '1987', 'journal-title': 'QCPE Bull.'}
/ QCPE Bull. by Schmidt M. W. (1987){'key': 'e_1_2_1_214_2', 'first-page': '10', 'volume': '9', 'author': 'Stewart J. J. P.', 'year': '1989', 'journal-title': 'QCPE Bull.'}
/ QCPE Bull. by Stewart J. J. P. (1989)10.1021/ja00399a063
10.1002/cber.19891221225
10.1002/cber.19891221226
- T.‐K.Ha B.Lamatsch G.Slucky D.Secbach previously unpublished calculations.
{'key': 'e_1_2_1_217_2', 'first-page': '85', 'volume': '2', 'author': 'Wiberg K. B.', 'year': '1989', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Wiberg K. B. (1989)- W. J.Hehre C. F.Pau S. D.Kahn R. F.Hout Jr. M. M.Francl:Molecular Modeling Computer‐Aided Descriptions of Molecular Structure and Reactivity Wiley New York in press (promised in footnote 10b of [220]).
10.1007/BFb0048506
{'key': 'e_1_2_1_219_3', 'first-page': '247', 'volume-title': 'Stereochemistry of Organic and Bioorganic Transformations, Workshop Conferences Hoechst', 'author': 'Houk K. N.', 'year': '1987'}
/ Stereochemistry of Organic and Bioorganic Transformations, Workshop Conferences Hoechst by Houk K. N. (1987)10.1021/ja00237a051
10.1021/ja00252a062
10.1021/ja00222a019
10.1021/ja00219a067
10.1021/jo00289a020
10.1021/ja00270a044
10.1021/ja00222a022
10.1021/ja00389a045
10.1002/ange.19891010305
10.1002/anie.198902681
10.1021/ar00161a004
10.1107/S0021889888009550
10.1002/prot.340030402
10.1021/bi00415a001
10.1093/protein/2.1.5
- “Dynamic simulation of complex molecular systems”:H. J. C.Berendsen W. F.van Gunsteren E.Egberts;
10.1021/bk-1987-0353.ch007
10.1111/j.1749-6632.1986.tb20961.x
10.1111/j.1749-6632.1986.tb20962.x
10.1002/hlca.19820650141
{'key': 'e_1_2_1_228_3', 'first-page': '632', 'volume': '21', 'author': 'Seebach D.', 'year': '1985', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by Seebach D. (1985){'key': 'e_1_2_1_228_4', 'first-page': '147', 'volume': '39', 'year': '1985', 'journal-title': 'Chimia'}
/ Chimia (1985)10.1002/hlca.19330160177
10.1002/hlca.19340170136
10.1002/hlca.19340170157
- P. A.Holmes L. F.Wright S. H.Collins Eur. Pat. Appl. EP 52 459 (1982);Imperial Chemical Industries PLC;
{'key': 'e_1_2_1_230_3', 'first-page': '143146 r', 'volume': '97', 'year': '1982', 'journal-title': 'Chem. Abstr.'}
/ Chem. Abstr. (1982){'key': 'e_1_2_1_231_2', 'first-page': '954', 'volume': '1983', 'author': 'Ballard D. G. H.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Ballard D. G. H.- S. C.Taylor Eur. Pat. Appl. EP 76 606 (1983);Imperial Chemical Industries PLC;
{'key': 'e_1_2_1_231_4', 'first-page': '103704f', 'volume': '99', 'year': '1989', 'journal-title': 'Chem. Abstr.'}
/ Chem. Abstr. (1989)10.1002/ange.19850970205
10.1002/anie.198500773
{'key': 'e_1_2_1_233_2', 'first-page': '129', 'volume-title': 'Chemieforschung im Degussa‐Forschungszentrum Wolfgang', 'author': 'Drauz K.', 'year': '1988'}
/ Chemieforschung im Degussa‐Forschungszentrum Wolfgang by Drauz K. (1988)10.1007/978-3-642-83758-6_4
{'key': 'e_1_2_1_234_3', 'first-page': '97', 'volume': '21', 'author': 'Laszlo P.', 'year': '1988', 'journal-title': 'Aldrichimica Acta'}
/ Aldrichimica Acta by Laszlo P. (1988){'key': 'e_1_2_1_234_4', 'volume-title': 'Pre‐parative Chemistry Using Supported Reagents', 'author': 'Laszlo P.', 'year': '1987'}
/ Pre‐parative Chemistry Using Supported Reagents by Laszlo P. (1987)- see also the use of Al2 O3for nitroaldol additions in [104d] (Rosini Ballinit).
10.1007/3-540-19180-1_5
10.1002/ciuz.19890230503
- Top. Curr. Chem. 1987 142
- Top. Curr. Chem. 1988 143
- Top. Curr. Chem. 1988 148
- Top. Curr. Chem. 1990 152
10.1007/978-3-642-69493-6
{'key': 'e_1_2_1_238_3', 'volume-title': 'Electroorganic Syntheses. Part I: Oxidations', 'author': 'Torii S.', 'year': '1985'}
/ Electroorganic Syntheses. Part I: Oxidations by Torii S. (1985){'issue': '2', 'key': 'e_1_2_1_238_4', 'first-page': '17', 'volume': '1987', 'author': 'Scháfer H. J.', 'journal-title': 'Kontakte (Darmstadt)'}
/ Kontakte (Darmstadt) by Scháfer H. J.{'issue': '3', 'key': 'e_1_2_1_238_5', 'first-page': '37', 'volume': '1987', 'journal-title': 'Kontakte (Darmstadt)'}
/ Kontakte (Darmstadt){'key': 'e_1_2_1_238_6', 'volume-title': 'Synthetic Organic Electrochemistry', 'author': 'Fry A. J.', 'year': '1989'}
/ Synthetic Organic Electrochemistry by Fry A. J. (1989)10.1002/hlca.19890720302
10.1007/3-540-17871-6_11
10.1002/ange.19850970705
10.1002/anie.198505391
{'key': 'e_1_2_1_241_4', 'first-page': '1071', 'volume': '1989', 'author': 'Thompson K.', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by Thompson K.10.1002/ciuz.19890230205
{'key': 'e_1_2_1_242_3', 'volume-title': 'High Pressure Chemical Synthesis', 'author': 'Jurczak J.', 'year': '1989'}
/ High Pressure Chemical Synthesis by Jurczak J. (1989){'key': 'e_1_2_1_242_4', 'volume-title': 'Organic High Pressure Chemistry', 'author': 'Le Noble W. J.', 'year': '1988'}
/ Organic High Pressure Chemistry by Le Noble W. J. (1988)- see also the high‐pressure chapter in [249]
{'key': 'e_1_2_1_243_2', 'first-page': '449', 'volume': '37', 'author': 'Seebach D.', 'year': '1983', 'journal-title': 'Chimia'}
/ Chimia by Seebach D. (1983)10.1007/BFb0071301
10.1002/ange.19770890307
10.1002/anie.197701253
- (d) “Crystal Structures and Stereoselective Reactions of Organic Lithium Derivatives”:D.Seebach Proc. Robert A. Welch Found Conf. Chem. Res. 27: Stereospecificity in Chemistry and Biochemistry 7–9 Nov. 1983 Houston. TX 1984 pp. 93–141;
{'key': 'e_1_2_1_243_7', 'first-page': '150', 'volume': '43', 'author': 'Wynberg H.', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia by Wynberg H. (1989)- (f) see the “principle of isoinversion” and suggestions for establishing optimal conditions in complex reaction phenomena [253] as well as the Curtin–Hammett principle (textbooks of physical organic chemistry) originally formulated for conformational pre‐equilibria.
- “Small Scale Continuous Processes”:E.Galantay lecture at thePMA Spring Symposium Charlottesville VA. 17–20 April 1988 (Bulk Pharmaceutical Operations—the Challenge of the Nineties). I wish to thank Dr.Galantay(Sandoz Pharma AG. Basel) for providing the pictures included in Fig. 11.
- Z.Brich H.Mühle Eur. Pat. Appl. EP 48 695 (1982) Sandoz AG;
{'key': 'e_1_2_1_245_3', 'first-page': '72651p', 'volume': '97', 'year': '1982', 'journal-title': 'Chem. Abstr.'}
/ Chem. Abstr. (1982)10.1135/cccc19831333
10.1021/ja00199a054
- Lithiation of dithianes is normally carried out atca.−20 °C in THF. The resulting solutions can be kept for some time in the refrigerator.
{'key': 'e_1_2_1_249_2', 'first-page': '103', 'volume-title': 'Organic Synthesis—Theory and Applications, A Research Annual', 'author': 'Giguere R. J.', 'year': '1989'}
/ Organic Synthesis—Theory and Applications, A Research Annual by Giguere R. J. (1989)10.1002/hlca.19730560609
10.1002/ange.19891010907
10.1002/anie.198911931
10.1002/nadc.19850330307
10.1126/science.4038558
10.1021/ja00196a048
{'key': 'e_1_2_1_254_2', 'first-page': '226', 'volume-title': 'Photochemistry in Organic Synthesis', 'author': 'Wendcr P. A.', 'year': '1986'}
/ Photochemistry in Organic Synthesis by Wendcr P. A. (1986)10.1007/978-3-642-82805-8_2
10.1002/9780470771662.ch10
10.1021/jo00233a001
10.1039/cs9881700283
10.1021/ar00149a005
10.1021/ar00155a005
10.1002/ange.19881001008
10.1002/anie.198812273
10.1002/nadc.19850330406
/ Nachr. Chem. Tech. Lab by Braun M. (1985)- see also [344–346].
{'key': 'e_1_2_1_256_2', 'volume-title': 'Radicals in Organic Synthesis: Formation of Carbon‐Carbon Bonds', 'author': 'Giese B.', 'year': '1986'}
/ Radicals in Organic Synthesis: Formation of Carbon‐Carbon Bonds by Giese B. (1986)10.1002/ange.19891010804
10.1002/anie.198909693
10.1055/s-1988-27600
/ Synthesis by Curran D. P.10.1021/jo00250a051
10.1021/jo00271a058
10.1016/S0040-4039(01)80281-1
10.1055/s-1990-20996
10.1002/hlca.19890720502
-
F.Cardinaux A.Thaler D.Seebach Helv. Chim. Acta74(1991) in press.
(
10.1002/hlca.19910740319
) - J. C.Hendrix K. J.Halverson J. T.Jarrett P. T.Lansbury Jr. J. Am. Chem. Soc.112(1990) in press. I wish to thank ProfessorPeter Lansburyfor providing me with the manuscript prior to the publication of this work and for permission to mention his results.
{'key': 'e_1_2_1_262_2', 'volume-title': 'Syntheses and separations using functional polymers', 'author': 'Sherrington D. C.', 'year': '1988'}
/ Syntheses and separations using functional polymers by Sherrington D. C. (1988)10.1351/pac198860030415
10.1016/S0065-3055(08)60113-6
10.1002/nadc.19870350805
- ICCOSS IX 9th International Conference on the Chemistry of the Organic Solid State Villa Olmo. Como (Italy). 2–7 July 1989 Abstracts.
{'key': 'e_1_2_1_265_2', 'volume-title': 'Organic Solid State Chemistry', 'author': 'Desiraju G. R.', 'year': '1987'}
/ Organic Solid State Chemistry by Desiraju G. R. (1987)10.5059/yukigoseikyokaishi.47.1118
10.1021/jo00274a007
{'key': 'e_1_2_1_267_3', 'first-page': '958', 'volume': '1988', 'author': 'Toda F.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Toda F.10.1002/ange.19891010317
10.1002/anie.198903201
{'key': 'e_1_2_1_269_2', 'first-page': '209', 'volume': '1989', 'author': 'Toda F.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Toda F.{'key': 'e_1_2_1_270_2', 'first-page': '1245', 'volume': '1989', 'author': 'Toda F.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Toda F.- Both the dioxolane derivative used here and its enantiomer are accessible in two steps from (R R)‐ or (S S)‐tartaric acid. It was first used as a ligand in the enantioselective addition to aldehydes via alkyl titanium compounds [273 274] and later also for the TiX4‐mediated Diels—Alder reaction [275] (see also Scheme 22 enantioselective catalysis and Sec. 7). Preparation of the compound has been described in detail [274 275].
10.1351/pac198355111807
10.1002/ange.19830950103
10.1002/anie.198300311
{'key': 'e_1_2_1_272_5', 'first-page': '77', 'volume-title': 'Organic Synthesis: an interdisciplinary challenge', 'author': 'Seebach D.', 'year': '1985'}
/ Organic Synthesis: an interdisciplinary challenge by Seebach D. (1985){'key': 'e_1_2_1_273_2', 'first-page': '217', 'volume': '3', 'author': 'See‐bach D.', 'year': '1983', 'journal-title': 'Mod. Synth. Methods'}
/ Mod. Synth. Methods by See‐bach D. (1983)10.1002/hlca.19870700406
10.1002/hlca.19790620604
10.1002/hlca.19790620819
10.15227/orgsyn.061.0042
10.1021/jo00320a014
- Chiral Li amides used in preparing enolates and for other lithiations . also lead to chiral amines in the reaction mixture and they can influence the stcric course of reactions: see the discussion in [172] (Sec 4.3. ref. (259–278);
10.1021/ja00203a032
10.1007/978-3-642-82805-8_1
10.1055/s-1989-27398
{'key': 'e_1_2_1_279_3', 'first-page': '31', 'volume': '21', 'author': 'Abdulla R. F.', 'year': '1988', 'journal-title': 'Aldrichimica Acta'}
/ Aldrichimica Acta by Abdulla R. F. (1988)10.1002/nadc.19860341206
/ Nachr. Chem. Tech. Lab. by Reis‐sig H.‐U. (1986)10.1016/0022-328X(87)85005-2
10.1021/jo00274a025
10.1002/ange.19840960712
10.1002/anie.198405321
10.1021/jo00249a036
{'key': 'e_1_2_1_283_3', 'first-page': '500', 'volume': '1988', 'author': 'Brandes E.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Brandes E.10.1016/S0040-4020(01)89795-7
- E.Winterfeldonce said: “It has certainly been good for synthetic chemistry that natural product synthesis has consistently set increasingly ambitious goals thereby subjecting newcomers on the ‘methods’ market to a swift baptism by fire” (lecture:25 Jahre Organische Chemie—Entwicklun‐gen und Tendenzen 125th anniversary of Hoechst Scientific Symposium 19–20 May 1988 Festschrift pp. 42–54).
- In June 1990 within the context of the “Joint 45th Northwest/ 10th Rocky Mountains Regional Meeting—American Chemical Society” in Salt Lake City. UT there was a symposium with the title “Posi‐Modern Organic Synthesis—Methods for the 1990s”. A glance at the lecture topics failed to provide for me any revealing visions of the future. I wish to thank Dr.Janet Grissomfor sending me a copy of the program prior to its actual release.
- …A. E.andI. U.
10.1351/pac198860111573
- For recent general reviews of Si chemistry in organic synthesis see [109] and: “Organosilicon Chemistry in Organic Synthesis” Tetrahedron Sym‐posia‐in‐Print Number 32:
10.1016/S0040-4020(01)86633-3
10.1016/0040-4020(82)87002-6
10.1055/s-1982-29685
10.1021/cr00075a001
{'key': 'e_1_2_1_292_2', 'first-page': '1805', 'volume': '1984', 'author': 'Fleming I.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Fleming I.10.1055/s-1987-27937
10.1002/ange.19881001223
10.1002/anie.198817181
- Chem. Ber.123(1990) in press.
{'key': 'e_1_2_1_294_2', 'first-page': '295', 'volume': '7', 'author': 'Peterson D. J.', 'year': '1971', 'journal-title': 'Organomet. Chem. Rev. Sect. A'}
/ Organomet. Chem. Rev. Sect. A by Peterson D. J. (1971){'key': 'e_1_2_1_295_2', 'first-page': '2825', 'volume': '1975', 'author': 'Utimoto K.', 'journal-title': 'Tetrahedron Lett.'}
/ Tetrahedron Lett. by Utimoto K.10.1021/om50005a041
10.1016/S0040-4039(00)95587-4
10.1002/nadc.19890370308
10.1016/S0040-4039(00)74575-8
10.1039/cs9760500377
10.1002/hlca.19870700226
10.1002/jlac.1990199001129
10.1055/s-1971-21707
/ Synthesis by Rühlmann K{'key': 'e_1_2_1_300_3', 'first-page': '259', 'volume': '23', 'author': 'Bloomfield J. J.', 'year': '1976', 'journal-title': 'Org. React. (N. Y.)'}
/ Org. React. (N. Y.) by Bloomfield J. J. (1976)10.1055/s-1990-20995
- “Trimethylsilylazid”: Kontakte (Darmstadt/1987. No. 2. pp. 14–15 and references cited therein.
10.1016/S0040-4020(01)89490-4
10.5059/yukigoseikyokaishi.44.149
10.1002/hlca.19880710120
10.1002/hlca.19880710121
10.1021/ja00799a072
10.1002/ange.19810930433
10.1002/anie.198103971
10.1002/hlca.19820650402
- see also the book by Torssell cited in (104c).
10.1055/s-1984-30849
{'key': 'e_1_2_1_308_3', 'first-page': '1', 'volume': '38', 'author': 'Ager D. J.', 'year': '1990', 'journal-title': 'Org. React. (N. Y.)'}
/ Org. React. (N. Y.) by Ager D. J. (1990)10.1021/jo00275a003
10.1002/cber.19781110807
10.1016/S0040-4020(01)86666-7
10.5059/yukigoseikyokaishi.46.367
10.1016/S0040-4039(00)87960-5
{'key': 'e_1_2_1_311_3', 'first-page': '5903', 'volume': '28', 'author': 'Tokitoh N.', 'year': '1987', 'journal-title': 'Yuki Goxei Kagaku Kyokaishi (J. Synth. Org. them. Jpn)'}
/ Yuki Goxei Kagaku Kyokaishi (J. Synth. Org. them. Jpn) by Tokitoh N. (1987){'key': 'e_1_2_1_311_4', 'first-page': '314', 'volume': '43', 'author': 'Seebach D.', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia by Seebach D. (1989){'key': 'e_1_2_1_312_2', 'first-page': '211', 'volume': '118', 'author': 'Dondoni A.', 'year': '1988', 'journal-title': 'Gaz Chim Ital.'}
/ Gaz Chim Ital. by Dondoni A. (1988)10.1002/ange.19760882103
10.1002/anie.197606391
10.1002/ciuz.19870210404
10.1002/ciuz.19890230304
10.1021/ja00292a008
10.1021/ja00185a005
10.1016/S0040-4020(01)88362-9
10.1002/nadc.19870350307
10.1021/ar00149a004
10.1055/s-1988-27540
{'key': 'e_1_2_1_315_6', 'first-page': '1', 'volume': '1989', 'author': 'Sakurai H.', 'journal-title': 'Synlett'}
/ Synlett by Sakurai H.10.1002/0471264180.or037.02
{'key': 'e_1_2_1_315_8', 'first-page': '173', 'volume-title': 'Organic. Synthesis—Theory and Applications. A Research Annual', 'author': 'Majetich G.', 'year': '1989'}
/ Organic. Synthesis—Theory and Applications. A Research Annual by Majetich G. (1989)10.1002/ange.19850970923
10.1002/anie.198507651
10.1016/S0040-4039(00)94167-4
10.1002/ijch.198900042
10.1021/ja00737a057
{'key': 'e_1_2_1_319_2', 'first-page': '119', 'volume': '1984', 'author': 'Fleming I.', 'journal-title': 'J. Chem. Soc. Perkin Trans. 1'}
/ J. Chem. Soc. Perkin Trans. 1 by Fleming I.{'key': 'e_1_2_1_320_2', 'first-page': '460', 'volume': '1982', 'author': 'Isaac K.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Isaac K.10.1021/ja00277a028
- see also [311].
10.1002/cber.19891221225
10.1002/cber.19891221226
10.1021/ja00345a082
{'key': 'e_1_2_1_324_2', 'first-page': '802', 'volume': '1983', 'author': 'Yamamoto Y.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Yamamoto Y.10.1016/S0040-4039(00)99469-3
10.1002/cber.19851180137
10.1021/ja00248a045
{'key': 'e_1_2_1_325_5', 'first-page': '1302', 'volume': '1987', 'author': 'Yamada J.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Yamada J.- see also Sec. 7.2.2 enantioseleetive carbonyl addition of organolead compounds under the influence of chiral catalysts.
10.1021/jo00270a001
10.1039/cs9871600045
10.1016/S0040-4039(00)86664-2
10.1016/0040-4039(88)85285-7
10.5059/yukigoseikyokaishi.45.603
{'key': 'e_1_2_1_327_4', 'first-page': '1', 'volume': '1980', 'author': 'Petragnani N.', 'journal-title': 'Synthesis'}
/ Synthesis by Petragnani N.10.1021/ar00117a003
10.1002/cber.19751080139
10.1016/0040-4020(82)85090-4
10.1002/ange.19881000406
10.1002/anie.198804791
10.1002/ange.19650770303
10.1002/anie.196501211
{'key': 'e_1_2_1_329_4', 'first-page': '1', 'volume-title': 'Methoden der Organischem Chemie (Houben‐Weyl)', 'author': 'Seebach D.', 'year': '1971'}
/ Methoden der Organischem Chemie (Houben‐Weyl) by Seebach D. (1971)- (b) on the other hand the formerCorey‐coworkerD. S.[18.31] is fascinated by the host of developments since 1976 [330c] in the area of applications of sulfur and selenium compounds in organic synthesis stemming directly from the laboratories of formerCorey‐group members. A few examples are cited under [330d];
{'key': 'e_1_2_1_329_6', 'first-page': '173', 'volume': '1', 'author': 'Seebach D.', 'year': '1976', 'journal-title': 'Mod. Synth. Methods'}
/ Mod. Synth. Methods by Seebach D. (1976)10.1021/ja00190a064
10.1016/S0040-4020(01)85823-3
10.1021/ja00215a076
- see also the review article byP. Fuchset al. in [376];
{'key': 'e_1_2_1_329_11', 'volume-title': 'Organoselenium Chemistry 1. Functional Group Transformations', 'author': 'Krief A.', 'year': '1988'}
/ Organoselenium Chemistry 1. Functional Group Transformations by Krief A. (1988)10.1021/ja00199a031
10.1002/0470034386.ch16
- “Total Synthesis Mediated by Cyclic Sulfides”:E.Vedejs article for the book by E. Block (Ed.):Organic Synthesis—Theory and Application JAI Press Greenwich in press;
- I wish to thank ProfessorEdwin Vedejsfor providing me with a manuscript copy.
- (a) The following book is an excellent source of information and discussion of the fundamental contributions byMukaiyama:T.Mukaiyama:Organic Synthetic Reactions Tokyo Kagakudojin 1987;
{'key': 'e_1_2_1_330_3', 'series-title': 'Int. Ser. Monographs on Chemistry No. 20', 'volume-title': 'Challenges in Synthetic Organic Chemistry', 'year': '1990'}
/ Challenges in Synthetic Organic Chemistry / Int. Ser. Monographs on Chemistry No. 20 (1990)10.1002/0471264180.or028.03
/ Org. React. (N. Y.) by Mukaiyama T. (1982)10.1016/B978-0-12-507703-3.50007-5
- (d) most recent comprehensive review: “Recent Developments in Stereoselective Aldol Reactions”:M.Braunin V. Snieckus (Ed.):Advances in Carbanion Chemistry JAI Press Greenwich CT 1990 in press;
10.1002/ange.19870990106
10.1002/anie.198700241
- M.Braun D.Waldmüller H.Sacha Chemie‐dozententagung 1990 Ulm 26–28 March 1990 Wissenschaftliches Program und Vortragsreferate Universitátsverlag Ulm A 33;
- (e) for diastereoselective nitroaldol additions see [308].
10.1002/ange.19850970807
10.1002/anie.198506681
{'key': 'e_1_2_1_331_4', 'first-page': '1', 'volume': '35', 'author': 'Gawley R. E.', 'year': '1988', 'journal-title': 'Org. React. (N. Y.)'}
/ Org. React. (N. Y.) by Gawley R. E. (1988)10.1021/ja00426a033
10.1002/nadc.19880360507
/ Nachr. Chem. Tech. Lab. by Altenbach H.‐J. (1988)10.1002/nadc.19880360612
10.1021/cr00090a001
10.1055/s-1989-27158
10.1021/ja00849a054
10.1021/ja00206a017
{'key': 'e_1_2_1_333_5', 'first-page': '67', 'volume': '1990', 'author': 'Paquette L. A.', 'journal-title': 'Syn‐lett'}
/ Syn‐lett by Paquette L. A.10.1002/ange.19770890105
10.1002/anie.197700101
10.1002/ange.19840961105
10.1002/anie.198408761
10.1039/CS9871600187
10.1021/jo00279a021
10.1055/s-1987-27894
{'key': 'e_1_2_1_334_9', 'first-page': '192', 'volume': '1', 'author': 'Ganem B.', 'year': '1988', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Ganem B. (1988)10.1021/jo00239a024
10.1002/cber.19891220410
10.1002/jlac.199019900146
/ Liebigs Ann. Chem.- see also the enantioselective Diels Alder reactions in Sec. 7.2.2 and the “all‐carbon” Diels‐Alder reactions of Danishefsky dienes cited in [372].
- (a) “Intramolecular Mannich and Related Reactions”:L. E.Overman D. J.Riccain [349];
{'key': 'e_1_2_1_335_3', 'first-page': '271', 'volume': '32', 'author': 'Hiemstra H.', 'year': '1988', 'journal-title': 'Alkaloids (N. Y.)'}
/ Alkaloids (N. Y.) by Hiemstra H. (1988)10.1002/nadc.19890370408
10.1016/S0040-4020(01)89752-0
10.1021/jo00288a028
10.1021/jo00288a027
10.1002/9780470147283.ch5
- (b) Michael additions under the various conditions of the Mukaiyama aldolization are collected in chapters 9 and 13 of [331a];
10.1002/cber.19751080615
10.1002/hlca.19800630727
10.1002/hlca.19810640518
10.1002/hlca.19820650537
10.1002/cber.19831160616
{'key': 'e_1_2_1_336_11', 'first-page': '255', 'volume': '38', 'author': 'Häner R.', 'year': '1984', 'journal-title': 'Chimia'}
/ Chimia by Häner R. (1984)10.1002/hlca.19850680120
10.1002/hlca.19850680611
10.1139/v87-142
10.1002/hlca.19880710102
{'key': 'e_1_2_1_336_16', 'first-page': '1981', 'volume': '44', 'author': 'Brook M. A.', 'year': '1988', 'journal-title': 'Acta Crystallogr. Sect.'}
/ Acta Crystallogr. Sect. by Brook M. A. (1988)- see also the papers cited here of investigations by the research group ofRisalitiandValentin(Trieste) into the reactions of enamines with nitroolefins. For reviews of the reactions of nitroolefins see[105a] (Kabalka Barrett);
10.1002/cber.19751080617
10.1016/S0040-4039(00)86987-7
{'key': 'e_1_2_1_336_20', 'first-page': '183', 'volume': '39', 'author': 'Seebach D.', 'year': '1985', 'journal-title': 'Chimia'}
/ Chimia by Seebach D. (1985)10.1021/ja00177a026
10.1021/ja00186a068
10.1021/ja00166a026
10.1080/03086648508073398
{'key': 'e_1_2_1_338_2', 'first-page': '865', 'volume': '23', 'author': 'de Meijere A.', 'year': '1987', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by de Meijere A. (1987)10.1039/cs9881700229
10.1002/ange.19881000607
10.1002/anie.198807971
10.1007/978-94-009-0929-8
- and the articles therein byL. Ghosez(pp. 235–254) H.‐U Reissig(pp. 51–58) andB. M. Trost(pp. 1–23);
- (e) “Strain‐Assisted Syntheses”: Tetrahedron Symposia‐in‐Print Number 38:
10.1016/S0040-4020(01)80116-2
10.1021/ar00162a002
10.1016/S0040-4020(01)89102-X
10.1055/s-1990-20975
{'key': 'e_1_2_1_339_2', 'first-page': '129', 'volume': '1', 'author': 'Curran D. P.', 'year': '1988', 'journal-title': 'Adv. Cycloaddit.'}
/ Adv. Cycloaddit. by Curran D. P. (1988)10.1002/nadc.19840321006
- (c) Mukaiyama methods for preparing nitrile oxides from nitroalkanes: Chapter 2 in [331a]:
{'key': 'e_1_2_1_339_5', 'volume-title': '1,3‐Dipolar Cycloaddition Chemistry', 'author': 'Padwa A.', 'year': '1984'}
/ 1,3‐Dipolar Cycloaddition Chemistry by Padwa A. (1984){'key': 'e_1_2_1_340_2', 'first-page': '1', 'volume': '26', 'author': 'Gschwend H. W.', 'year': '1979', 'journal-title': 'Org. React. (N. Y)'}
/ Org. React. (N. Y) by Gschwend H. W. (1979)10.1002/nadc.19850330106
/ Nachr. Chem. Tech. Lab. by Braun M. (1985)10.1021/ar00131a005
10.1007/3-540-16931-8_8
{'key': 'e_1_2_1_340_6', 'first-page': '67', 'volume': '1998', 'author': 'Snieckus V.', 'journal-title': 'Bull. Soc. Chim. Fr.'}
/ Bull. Soc. Chim. Fr. by Snieckus V.10.1021/ja00246a059
10.1021/ja00164a025
10.1021/ja00164a026
10.1021/cr00097a007
10.1016/S0040-4020(01)86132-9
{'key': 'e_1_2_1_341_7', 'first-page': '39', 'volume': '43', 'author': 'Betschart C.', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia by Betschart C. (1989)10.1055/s-1989-27424
/ Synthesis by Lenoir D.10.1002/ange.19830950903
10.1002/anie.198306373
10.1002/hlca.19870700326
{'key': 'e_1_2_1_343_2', 'first-page': '281', 'volume-title': 'Selectivity—a Goal for Synthetic Efficiency, Workshop Conferences Hoechst', 'author': 'Stork G.', 'year': '1984'}
/ Selectivity—a Goal for Synthetic Efficiency, Workshop Conferences Hoechst by Stork G. (1984)10.1021/ar00113a004
10.1055/s-1987-28044
10.1351/pac198860111549
{'key': 'e_1_2_1_345_4', 'first-page': '3', 'volume': '23', 'author': 'Barton D. H. R.', 'year': '1990', 'journal-title': 'Aldrichimica Acta'}
/ Aldrichimica Acta by Barton D. H. R. (1990)10.1055/s-1981-29317
10.1021/jo00228a016
10.1021/ar00160a006
- see also the review article byE. Blocket al. in [330d].
- The most complete up‐to‐date review of the current state of organic synthesis will be provided by the eight‐volume workComprehensive Organic Synthesis(B. M. Trost Ed.) Pergamon Press London which is to be released this year.
- Diastereoselectivity is at the heart of a series of seven essays byE. Winter‐feldtpublished between 1985 and 1987 in the Merck magazineKontakte (Darmstadt) which have in the meantime appeared in book form: E. Winterfeldt:Prinzipen und Methoden der Stereoselektiven Synthese Vieweg Braunschweig 1988. The Diels–Alder reaction the Claisen–Cope rearrangement the aldol and Michael additions stereoselective additions to carbonyl groups and the utilization of small rings are all subjects of extensive discussion (altogether over 800 references).
- … often referred to as “tandem reactions” “multiple‐component coupling” or “multiply convergent reactions”.
{'key': 'e_1_2_1_351_2', 'first-page': '91', 'volume': '2', 'author': 'Seebach D.', 'year': '1980', 'journal-title': 'Mod. Synth. Methods'}
/ Mod. Synth. Methods by Seebach D. (1980)10.1007/978-3-642-82805-8_4
{'key': 'e_1_2_1_353_2', 'first-page': '85', 'volume-title': 'Stereochemistry of Organic and Bioorganic Transformations. Workshop Conferences Hoechst', 'author': 'Seebach D.', 'year': '1987'}
/ Stereochemistry of Organic and Bioorganic Transformations. Workshop Conferences Hoechst by Seebach D. (1987){'key': 'e_1_2_1_354_2', 'volume-title': 'Methods for the Oxidation of Organic Compounds. Alcohols. Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes', 'author': 'Haines A. H.', 'year': '1988'}
/ Methods for the Oxidation of Organic Compounds. Alcohols. Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes by Haines A. H. (1988)10.1016/S0040-4039(00)98245-5
10.1021/jo01298a066
10.1016/S0040-4039(00)85677-4
{'key': 'e_1_2_1_357_2', 'first-page': '3', 'volume-title': 'Methoden der Organischen Chemie (Houben‐Weyl). Vol. VIII, Sauerstoffverbindungen III', 'author': 'Criegee R.', 'year': '1952'}
/ Methoden der Organischen Chemie (Houben‐Weyl). Vol. VIII, Sauerstoffverbindungen III by Criegee R. (1952){'key': 'e_1_2_1_357_3', 'first-page': '1143', 'volume-title': 'Methoden der Organischen Chemie (Houben‐Weyl). Vol. VIII, Sauerstoffverbindungen III, Vol. E 13', 'author': 'Zeller K. P.', 'year': '1988'}
/ Methoden der Organischen Chemie (Houben‐Weyl). Vol. VIII, Sauerstoffverbindungen III, Vol. E 13 by Zeller K. P. (1988)10.1021/ja01034a027
10.1021/ja01581a057
10.1021/ja01524a080
10.1002/cber.19360690842
10.1021/ja00986a031
{'key': 'e_1_2_1_360_3', 'first-page': '1', 'volume-title': 'Oxidation', 'author': 'Moffatt J. G.', 'year': '1971'}
/ Oxidation by Moffatt J. G. (1971)10.1021/ja00776a056
{'key': 'e_1_2_1_361_3', 'first-page': '919', 'volume': '1973', 'journal-title': 'Tetrahedron Lett.'}
/ Tetrahedron Lett.10.1016/0040-4020(78)80197-5
10.1055/s-1981-29377
{'key': 'e_1_2_1_364_2', 'volume-title': 'Modern Synthetic Reactions', 'author': 'House H. O.', 'year': '1972'}
/ Modern Synthetic Reactions by House H. O. (1972)10.1021/ja01018a051
10.1002/cber.19580910223
10.1002/hlca.19850680421
10.1351/pac198658040505
- See the work ofG.Wittig G.Stork A. I.Meyers E. J.Corey andD.Endersin chapter 6 of the following review: D. Seebach K.‐H. Geiss in D. Seyfert (Ed.): Proc. Symp. ACS Natl. Meet New York City 6–9 April 1976;
{'key': 'e_1_2_1_369_3', 'first-page': '1', 'volume': '1', 'year': '1976', 'journal-title': 'J. Organomet. Chem. Libr.'}
/ J. Organomet. Chem. Libr. (1976)- For the structure of a cyclopropanecarboxylic ester Li enolate and a discussion of its high reactivity see [167c] and references cited therein.
- W.Amberg:Substituierte β‐Hrdroxycarbonsäuren ans (2R 6R)‐2‐tert‐Butyl‐6‐methyl‐dioxanonderivaten Dissertation Nr. 9148.ETH Zürich 1990;
-
W.Amberg D.Seebach Chem. Ber.123(1990) in press.
(
10.1002/cber.19901231227
) {'key': 'e_1_2_1_372_2', 'first-page': '273', 'volume': '2', 'author': 'Danishefsky S.', 'year': '1989', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Danishefsky S. (1989)10.15227/orgsyn.061.0147
10.1002/ange.19870990105
10.1002/anie.198700151
- Trivial steps conducted prior to or following the actual in‐situ reaction sequence are implicitly included.
- MIMIRC forMichael‐Michael ringclosure MIMI‐MIRC fürMichael‐Michael‐Michael ringclosure or SMIRC for sequentialMichael ringclosure [375].
10.1021/cr00075a007
10.1021/cr00075a012
10.1021/ja00223a061
10.1016/S0040-4020(01)89799-4
10.1021/ja00223a026
10.1002/ange.19770890520
10.1002/anie.197703211
10.1002/hlca.19810640313
10.1002/hlca.19810640314
10.1021/jo00164a011
- P. A.Wender A. G.Olivero unpublished experiments mentioned in [254a].
10.1021/ja00961a052
{'key': 'e_1_2_1_382_2', 'first-page': '512', 'volume': '1966', 'author': 'Bryce‐Smith D.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Bryce‐Smith D.10.1016/S0040-4020(01)96707-9
- for additional examples of diastereoselective formation of pyrrolidine sec [340d].
{'key': 'e_1_2_1_384_2', 'first-page': '1047', 'volume': '1985', 'author': 'Hagiwara H.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Hagiwara H.{'key': 'e_1_2_1_385_2', 'first-page': '2559', 'volume': '1985', 'author': 'Hickmott P. W.', 'journal-title': 'J. Chem. Soc. Perkin Trans, 1'}
/ J. Chem. Soc. Perkin Trans, 1 by Hickmott P. W.10.1021/ja00263a029
10.1016/S0040-4020(01)93265-X
{'key': 'e_1_2_1_388_2', 'volume-title': 'Comprehensive Organometallic Chemistry', 'author': 'Wilkinson G.', 'year': '1982'}
/ Comprehensive Organometallic Chemistry by Wilkinson G. (1982){'key': 'e_1_2_1_389_2', 'volume-title': 'Modern Synthetic Methods', 'author': 'Scheffold R.', 'year': '1983'}
/ Modern Synthetic Methods by Scheffold R. (1983)10.1098/rsta.1988.0101
- Especially useful are the annual reviews organized according to metal or by group within the periodic table appearing as:Organometallic Chemistry Specialist periodical report) The Royal Society of Chemistry Burlington House London WlV OBN.
{'key': 'e_1_2_1_392_2', 'volume-title': 'Fachinformationszentrum Chemie GmbH, Gesellschaft Deutscher Chemiker, Bayer AG', 'author': 'Spanagel H. D.'}
/ Fachinformationszentrum Chemie GmbH, Gesellschaft Deutscher Chemiker, Bayer AG by Spanagel H. D.10.1002/ange.19820941002
10.1002/anie.198207110
{'key': 'e_1_2_1_394_2', 'volume-title': 'Principles anil Applications of Organotransition Metal Chemistry', 'author': 'Collman J. P.', 'year': '1987'}
/ Principles anil Applications of Organotransition Metal Chemistry by Collman J. P. (1987){'key': 'e_1_2_1_395_2', 'volume-title': 'Organometallic Syntheses', 'author': 'King R. B.', 'year': '1965'}
/ Organometallic Syntheses by King R. B. (1965){'key': 'e_1_2_1_395_3', 'volume-title': 'Transition metals in total synthesis.', 'author': 'Harrington P. J.', 'year': '1990'}
/ Transition metals in total synthesis. by Harrington P. J. (1990)10.1055/s-1990-20974
10.1002/ange.19840960808
10.1002/anie.198405871
10.1002/ange.19891010719
10.1002/anie.198909081
{'key': 'e_1_2_1_399_2', 'volume-title': 'Transition Metal Carbene Complexes', 'author': 'Dötz K. H.', 'year': '1983'}
/ Transition Metal Carbene Complexes by Dötz K. H. (1983){'key': 'e_1_2_1_399_3', 'first-page': '22', 'volume': '22', 'author': 'Reissig H.‐U.', 'year': '1986', 'journal-title': 'Nachr. Chem. Tech. Lab.'}
/ Nachr. Chem. Tech. Lab. by Reissig H.‐U. (1986)10.1002/nadc.19880361207
10.1021/ar00138a001
10.1007/978-3-642-83758-6_2
10.1039/cs9891800187
10.1021/ic00276a025
10.1002/nadc.19870350307
10.1002/ange.19760881204
10.1002/anie.197603331
{'key': 'e_1_2_1_404_4', 'first-page': '31', 'volume': '18', 'author': 'Negishi E.', 'year': '1985', 'journal-title': 'Aldrichimica Acta'}
/ Aldrichimica Acta by Negishi E. (1985)- For applications of the Suzuki coupling see [341e].
10.1021/ar00136a003
10.1002/ange.19891010906
10.1002/anie.198911731
10.1021/ar00170a004
10.1021/ar00093a004
{'key': 'e_1_2_1_407_3', 'first-page': '135', 'volume': '1', 'author': 'Bäckvall J.‐E.', 'year': '1989', 'journal-title': 'Adv. Met.‐Org. Chem.'}
/ Adv. Met.‐Org. Chem. by Bäckvall J.‐E. (1989)10.1002/ange.19891010106
10.1002/anie.198900381
10.1021/cr00093a002
{'key': 'e_1_2_1_409_2', 'first-page': '322', 'volume': '177', 'author': 'Reich M. R.', 'year': '1923', 'journal-title': 'Séances Acad. Sci.'}
/ Séances Acad. Sci. by Reich M. R. (1923)10.1002/recl.19360551003
10.1021/ja01854a005
{'key': 'e_1_2_1_410_2', 'volume-title': 'An Introduction to Synthesis Using Organocopper‐Reagents', 'author': 'Posner G. H.', 'year': '1980'}
/ An Introduction to Synthesis Using Organocopper‐Reagents by Posner G. H. (1980)- see also: “Recent Developments in Organocopper Chemistry”. Tetrahedron Symposia‐in‐Print Number 35:
10.1016/0040-4020(89)80063-8
10.1002/ange.19740862102
10.1002/anie.197407011
10.1002/ange.19860981102
10.1002/anie.198609473
10.5059/yukigoseikyokaishi.44.829
10.1021/ja00186a031
- (d) for the use of silylcuprates in the Michael addition of Si‐groups see [293 294];
10.1055/s-1990-21009
10.1016/0040-4020(80)80126-8
10.1016/S0040-4039(00)95113-X
10.1016/0040-4020(89)80064-X
10.1021/ja00282a052
10.1021/ja00241a021
10.1055/s-1989-27326
10.1021/ja00255a074
10.1021/om00087a015
10.1002/ange.19891010333
10.1002/anie.198903511
10.5059/yukigoseikyokaishi.47.931
10.1007/3-540-11766-0_1
10.1007/978-3-642-70704-9
10.1002/ange.19840960805
10.1002/anie.198405561
10.1002/hlca.19810640532
10.1016/S0040-4039(01)81404-0
10.3987/COM-88-S131
10.1016/S0040-4020(01)82098-6
10.5059/yukigoseikyokaishi.46.66
10.1002/hlca.19810640136
{'key': 'e_1_2_1_418_2', 'first-page': '180', 'volume': '67', 'author': 'Imwinkelried R.', 'year': '1988', 'journal-title': 'Org. Synth.'}
/ Org. Synth. by Imwinkelried R. (1988)10.1002/hlca.19810640755
10.1002/cber.19851180921
10.1002/ange.19891010425
10.1002/anie.198904941
10.1002/ange.19891010426
10.1002/anie.198904951
10.1002/ange.19891010427
10.1002/anie.198904971
10.1002/ange.19891010428
10.1002/anie.198904991
10.1002/hlca.19900730215
-
G.Bold R.Duthaler P.Herold W.Lottenbach K.Oertle M.Riediker G.Rihs A.Togni Lectures at theHerbstversammlung der Schweizerischen Chemischen Gesellschaft Bern. October 1989 Abstract Volume pp. 20 21 22.
(
10.1002/chin.198930105
) 10.1002/hlca.19840670612
10.1002/hlca.19870700826
10.1002/hlca.19880710818
10.1021/ja00202a053
10.1021/ja00255a073
{'key': 'e_1_2_1_427_2', 'first-page': '12', 'volume': '40', 'author': 'Raubenheimer H. G.', 'year': '1986', 'journal-title': 'Chimia'}
/ Chimia by Raubenheimer H. G. (1986)10.1021/ja00244a052
10.1021/ja00196a064
10.1016/S0040-4039(00)99038-5
10.1021/jo00362a052
{'key': 'e_1_2_1_431_2', 'first-page': '97', 'volume': '17', 'author': 'Hayakawa Y.', 'year': '1986', 'journal-title': 'Nucleic Acids Res. Symp. Ser.'}
/ Nucleic Acids Res. Symp. Ser. by Hayakawa Y. (1986){'key': 'e_1_2_1_431_3', 'first-page': '25', 'volume': '19', 'author': 'Mitsuhira Y.', 'year': '1988', 'journal-title': 'Nucleic Acids Res. Symp. Ser.'}
/ Nucleic Acids Res. Symp. Ser. by Mitsuhira Y. (1988){'key': 'e_1_2_1_431_4', 'first-page': '75', 'volume': '20', 'author': 'Hayakawa Y.', 'year': '1988', 'journal-title': 'Nucleic Acids Res. Symp. Ser.'}
/ Nucleic Acids Res. Symp. Ser. by Hayakawa Y. (1988)10.1021/ja00161a006
10.1351/pac199062040613
- I wish to thank ProfessorRyoji Noyorimost sincerely for providing me with manuscript copies prior to their publication [432 433] as well as for the chromatogram in Fig. 13 and permission to include these findings here.
{'key': 'e_1_2_1_435_2', 'first-page': '846', 'volume': '1988', 'author': 'Kagan H. B.', 'journal-title': 'Bull. Soc. Chim. Fr.'}
/ Bull. Soc. Chim. Fr. by Kagan H. B.- We suggested [352] in 1980 use of the abbreviation “EPC synthesis” as a generic term for the preparation of enantiomericallypurecompounds. While there might be disagreement over the definition of “purity” (which is dependent above all on the sensitivity of the analytical methods employed) the terminology is otherwise unambiguous. Expressions like “homochiral compounds” [437] or “isochiral compounds” [438] are unfortunate in several respects. Thus “homochiral” has long been used in comparing the chirality oftwosimilar compounds or a pair of chiral molecules in the unit cell of a crystal but it is now considered appropriate for describing a flask full of (+ )‐tartaric acid (1023molecules per mole)! Expressions like “chiral synthesis” and “racemic synthesis” have also become common; while these may be permissible in English (which also tolerates combinations like “married name” and “fishing pond”) they certainly cannot be translated directly into German. The equally correct expression “chiral not racemic” is more awkward than “enantiomerically pure”. Finally let me urge that the matter not be carried too far; in most cases all that is required is judicious use ofRorS!
10.1002/ange.19850970104
10.1002/anie.198500013
- Isochiral:Under discussion with respect to the preparation of a new edition of the classic textbook of stereochemistry byE. L.Eliel
10.1038/scientificamerican0190-108
{'issue': '3', 'key': 'e_1_2_1_439_3', 'first-page': '56', 'volume': '1990', 'journal-title': 'Spektrum Wiss.'}
/ Spektrum Wiss.10.1007/BF00541922
10.1002/9780470147283.ch4
- “Industrial Application of Asymmetric Synthesis” is the announced theme of the following conference:2nd Int. IUPAC Symp. Org. Chem. Technological Perspectives(Baden‐Baden April 1991).
10.1002/nadc.19760241704
/ Nachr. Chem. Tech. Lab. by Seebach D. (1976)10.1002/ange.19820940904
10.1002/anie.198206541
10.1002/ange.19820940805
10.1002/anie.198205671
- “Chiralily Recognition in Synthesis” (Fine Chemicals Group Society of Chemical Industry. London 1988). “Synthesis from Natural Homochiral Precursors” (Fine Chemicals Group Society of Chemical Industry. London 1990). “Second International Symposium on Chiral Discrimination” (Rome 1991).
- Chemistry in Britain. 1989
- As if there were not already enough periodicals‐and it were not already possible to present every good piece of work on the subject in one of the standard national or international chemical journals!
- Twenty years ago everything known about stereoselective reactions could be presented together in the single book byJ. D.MorrisonandH. S.Mosher:Asymmetric Organic Reactions Prentice Hall 1971 (ca. 450 pp.).
{'key': 'e_1_2_1_449_3', 'volume-title': 'Asymmetric Synthesis', 'year': '1983'}
/ Asymmetric Synthesis (1983)10.1016/S0040-4020(01)86036-1
10.1002/jlac.198919890293
10.1021/ja00306a045
{'key': 'e_1_2_1_453_2', 'first-page': '268', 'volume': '25', 'author': 'Davies S. G.', 'year': '1989', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by Davies S. G. (1989){'key': 'e_1_2_1_453_3', 'first-page': '608', 'volume': '1987', 'author': 'Davies S. G.', 'journal-title': 'Bull. Soc. Chim. Fr.'}
/ Bull. Soc. Chim. Fr. by Davies S. G.{'key': 'e_1_2_1_454_2', 'first-page': '59', 'volume': '18', 'author': 'Meyers A. I.', 'year': '1985', 'journal-title': 'Aldrichimica Acta'}
/ Aldrichimica Acta by Meyers A. I. (1985)10.1021/ja00263a051
{'key': 'e_1_2_1_455_3', 'first-page': '387', 'volume': '1988', 'author': 'Simpkins N. S.', 'journal-title': 'Chem. Ind. (London)'}
/ Chem. Ind. (London) by Simpkins N. S.10.1021/ja00208a025
{'key': 'e_1_2_1_457_2', 'first-page': '421', 'volume': '1984', 'author': 'Duhamel L.', 'journal-title': 'Bull. Soc. Chim. Fr. 11'}
/ Bull. Soc. Chim. Fr. 11 by Duhamel L.10.1021/ar00134a005
- see alsoG. H.Posnerin [350d].
10.1351/pac198860111699
10.1002/nadc.19870350307
10.1016/B978-0-12-507703-3.50009-9
10.1016/S0040-4020(01)86040-3
10.1007/978-3-642-82805-8_5
10.1016/B978-0-12-507703-3.50008-7
{'key': 'e_1_2_1_463_3', 'volume-title': 'Heterocycles in Organic Synthesis.', 'author': 'Meyers A. I.', 'year': '1974'}
/ Heterocycles in Organic Synthesis. by Meyers A. I. (1974)10.1002/9780470147221.ch1
10.1021/ja00300a054
10.1016/S0040-4039(00)95643-0
10.1016/S0040-4039(00)95305-X
10.1021/ja00212a037
10.1016/S0040-4020(01)86058-0
10.1021/ar00117a004
10.1016/S0040-4020(01)89149-3
10.1016/S0040-4039(01)80599-2
10.1021/ja00196a081
10.1021/ja00196a082
10.1021/ja00158a064
10.1021/ja00262a018
10.1016/S0040-4039(01)88993-0
10.1016/S0040-4020(01)80052-1
10.1021/ar00152a002
10.1055/s-1986-31845
10.1021/ar00152a001
{'key': 'e_1_2_1_470_3', 'first-page': '77', 'volume': '1', 'author': 'Brown H. C.', 'year': '1988', 'journal-title': 'Chemtracts: Org. Chem.'}
/ Chemtracts: Org. Chem. by Brown H. C. (1988){'key': 'e_1_2_1_470_4', 'volume-title': 'Borane Reapems', 'author': 'Pelter A.', 'year': '1988'}
/ Borane Reapems by Pelter A. (1988)10.1016/S0040-4020(01)86037-3
10.1021/ja00308a049
10.1016/S0040-4020(01)86780-6
10.1351/pac198860010039
10.1021/ja00163a045
10.1002/hlca.19880710527
10.1002/hlca.19870700819
10.1002/ange.19891010422
10.1002/anie.198904721
10.1002/hlca.19810640829
- “Synthesis of Chiral Non‐Racemic Compounds” Tetrahedron Symposia‐in‐Print Number 15:
10.1016/S0040-4020(01)82417-0
10.1016/0040-4020(80)80024-X
{'key': 'e_1_2_1_480_2', 'first-page': '293', 'volume': '53', 'author': 'Mori K.', 'year': '1985', 'journal-title': 'Spec. Publ. R. Soc. Chem.'}
/ Spec. Publ. R. Soc. Chem. by Mori K. (1985){'key': 'e_1_2_1_480_3', 'first-page': '677', 'volume': '1', 'author': 'Mori K.', 'year': '1988', 'journal-title': 'Stud. Nat. Prod. Chem'}
/ Stud. Nat. Prod. Chem by Mori K. (1988)10.5059/yukigoseikyokaishi.46.467
10.1016/S0040-4020(01)81007-3
10.1002/nadc.19840320211
10.1002/nadc.19880360109
10.1002/nadc.19870350307
10.5059/yukigoseikyokaishi.45.408
10.5059/yukigoseikyokaishi.45.1157
10.1038/scientificamerican0981-154
{'issue': '11', 'key': 'e_1_2_1_483_3', 'first-page': '88', 'volume': '1981', 'journal-title': 'Spektrum Wiss.'}
/ Spektrum Wiss.10.1126/science.221.4608.351
- Even a general‐circulation newspaper like DIE ZEIT (R. Schwerthöffer Die ZeitNo. 10 2 March 1990 p. 96) recently devoted a half page in its science section to the subjectThe Art of Catalysis(“Die Chemie nutzt natürliche Vorbilder”) mentioning among other thingsCorey's“Chemzymes”.
- Previously cited books and reviews covering biological‐chemical synthetic methods [79 114 125 126 241 354] A few additional more recent articles: (a) “Enzymes in Organic Syntheses”: J. B. Jones in F. E. C. S. Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Prod. (3.) VCH Verlagsgesellschaft Weinheim 1987 pp. 18–39;
10.1002/ange.19881000505
10.1002/anie.198806221
10.1002/ange.19891010605
10.1002/anie.198906951
10.1002/9780470147283.ch2
10.1055/s-1990-26775
{'key': 'e_1_2_1_487_2', 'first-page': '545', 'volume': '2', 'author': 'Levene P. A.', 'year': '1943', 'journal-title': 'Coll.'}
/ Coll. by Levene P. A. (1943){'key': 'e_1_2_1_487_3', 'first-page': '428', 'volume': '3', 'author': 'Helferich B.', 'year': '1955', 'journal-title': 'Coll.'}
/ Coll. by Helferich B. (1955){'key': 'e_1_2_1_487_4', 'first-page': '1', 'volume': '63', 'author': 'Seebach D.', 'year': '1985', 'journal-title': 'Coll.'}
/ Coll. by Seebach D. (1985){'key': 'e_1_2_1_487_5', 'first-page': '10', 'volume': '63', 'author': 'Jones J. B.', 'year': '1985', 'journal-title': 'Coll.'}
/ Coll. by Jones J. B. (1985){'key': 'e_1_2_1_487_6', 'first-page': '56', 'volume': '68', 'author': 'Mori K.', 'year': '1989', 'journal-title': 'Coll.'}
/ Coll. by Mori K. (1989){'key': 'e_1_2_1_487_7', 'first-page': '19', 'volume': '69', 'author': 'Eberle M.', 'year': '1990', 'journal-title': 'Coll.'}
/ Coll. by Eberle M. (1990){'key': 'e_1_2_1_488_2', 'first-page': '269', 'volume': '2', 'author': 'Fischli A.', 'year': '1980', 'journal-title': 'Mod. Synth. Method'}
/ Mod. Synth. Method by Fischli A. (1980)10.1007/978-3-642-83758-6_1
{'key': 'e_1_2_1_489_2', 'volume-title': 'Biotransformations in Preparative Organic Chemistry (The Use of Isolated Enzymes end Whole Cell Systems in Synthesis)', 'author': 'Davies H. G.', 'year': '1989'}
/ Biotransformations in Preparative Organic Chemistry (The Use of Isolated Enzymes end Whole Cell Systems in Synthesis) by Davies H. G. (1989)- Previously cited books and reviews on the topic of organometallic catalysis (263b 388 390 394 400 402 405–407 433 435) above all the articles byJ. K.Stille L. S.HegedusandR.Scheffoldin [389] and citations in Scheme 17.
{'key': 'e_1_2_1_490_3', 'first-page': '654', 'volume': '1988', 'author': 'Brunner H.', 'journal-title': 'Synthesis'}
/ Synthesis by Brunner H.10.1002/9780470147276.ch3
{'key': 'e_1_2_1_490_5', 'first-page': '276', 'volume': '25', 'author': 'Brown J. M.', 'year': '1989', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by Brown J. M. (1989)10.1016/S0040-4020(01)89159-6
10.1007/978-3-642-83758-6_3
{'key': 'e_1_2_1_491_2', 'volume-title': 'Catalysis of Organic Reactions', 'author': 'Blackburn D. W.', 'year': '1990'}
/ Catalysis of Organic Reactions by Blackburn D. W. (1990){'key': 'e_1_2_1_492_2', 'first-page': '359', 'volume': '33', 'author': 'Maryanoff C. A.', 'year': '1988', 'journal-title': 'Chem. Ind (Dekker)'}
/ Chem. Ind (Dekker) by Maryanoff C. A. (1988)- In other words biotechnology really is just an “old hat with new feathers” (H. Metz inMerck‐Spektrum.Switzerland No. 2. 1987).
- For example shikonin from the firm Mitsui Petrochemical Industries. Ltd. Iwakuni Yamaguchi‐ken 740 (Japan).
{'key': 'e_1_2_1_495_2', 'first-page': '1001', 'volume': '25', 'author': 'DiCosmo F.', 'year': '1989', 'journal-title': 'Chem. Br.'}
/ Chem. Br. by DiCosmo F. (1989)10.1016/S0022-1139(00)81968-5
10.1016/B978-1-4832-2718-4.50010-0
{'key': 'e_1_2_1_497_3', 'volume-title': 'Microbial transformations on non‐steroid cyclic compounds', 'author': 'Kieslich K.', 'year': '1976'}
/ Microbial transformations on non‐steroid cyclic compounds by Kieslich K. (1976)- Only papers of interest to the synthetic chemist have been considered [488b].
10.1002/hlca.19830660209
10.3109/10242429008992047
{'key': 'e_1_2_1_501_2', 'first-page': 'A554', 'volume': '60', 'author': 'Hess W. F.', 'year': '1988', 'journal-title': 'Chem. Ing. Tech.'}
/ Chem. Ing. Tech. by Hess W. F. (1988)- One need only consider the many possible conditions for an aldol addition (see [331] and Scheme 26) or for reduction with a complex hydride M1(M2H4‐nXn)b. in which M1= Li Na K Zn Bu4N M2= B Al X = RO RCOO R2N with n = 1–3 (there are entire books on the subject!).
10.1021/ja00356a041
10.1021/ja00296a038
{'key': 'e_1_2_1_504_2', 'first-page': '172', 'volume': '40', 'author': 'Ehrler J.', 'year': '1986', 'journal-title': 'Chimia'}
/ Chimia by Ehrler J. (1986){'key': 'e_1_2_1_504_3', 'first-page': '351', 'volume': '43', 'author': 'Haag T.', 'year': '1989', 'journal-title': 'Chimia'}
/ Chimia by Haag T. (1989)- For extensive competent discussions of the subject containing numerous literature citations see [486b e; 488b].
10.1002/ange.19840960222
10.1002/anie.198401511
10.1002/hlca.19850680420
10.1021/ja00299a044
10.1111/j.1749-6632.1987.tb45698.x
- Cubes of concentrated cell masses of the anaerobic microorganismThermoanaerobium brockiican be kept wrapped in aluminum foil in a freezer—like baker's yeast in a refrigerator—for long periods of time without loss of reductase activity [506b].
- Proteinogenic amino acids are produced in Japan either by fermentative techniques or by the enantioselective cleavage of amino acid derivatives with immobilized microorganisms or peptidase enzymes: “Production of Optically Active Amino Acids Using Immobilized Biocalalysts”:T.Tosa Int. Chem. Congr. Pacific Basin Societies 17–22 Dec. 1989 Honolulu HI. Abstr. ORGN 615.
- Degussa utilizes membrane techniques [233] cf. also [511]. Nevertheless much of the Degussa amino acid output is derived from protein hydrolyzates (animal skin hair horn hoof or feathers or protein‐containing material from plants) [233].
10.1021/jo00243a049
10.1007/978-94-011-2262-7_14
10.1021/ja00238a067
{'key': 'e_1_2_1_512_2', 'volume-title': 'Biocatalysis in Organic Media', 'author': 'Laane C.', 'year': '1987'}
/ Biocatalysis in Organic Media by Laane C. (1987)10.1002/ange.19650772412
{'key': 'e_1_2_1_513_3', 'first-page': '1079', 'volume': '4', 'year': '1965', 'journal-title': 'Angew. Chem. Int. Ed. Engl.'}
/ Angew. Chem. Int. Ed. Engl. (1965)10.1002/ange.19870990530
10.1002/anie.198704581
10.1016/S0040-4039(00)80529-8
10.1016/0006-291X(76)91020-2
10.1128/jb.129.3.1356-1364.1977
/ J. Bacteriology (1977)10.1016/S0040-4039(01)91382-6
10.1021/ja00222a035
{'key': 'e_1_2_1_515_2', 'first-page': '1815', 'volume': '1984', 'author': 'Kitazume T.', 'journal-title': 'Chem. Lett.'}
/ Chem. Lett. by Kitazume T.10.1007/978-94-009-4686-6_1
- Another case I would prefer to regard as a “youthful sin” (cf. Scheme 24b) is my suggestion [352]–taken up by many others as well–that this process be designated the “mesotrick”. Such expressions really should be confined to the—important! —realm of laboratory jargon.
10.1021/ja00323a043
10.1016/S0040-4039(00)85026-1
{'key': 'e_1_2_1_520_2', 'first-page': '469', 'volume': '1977', 'author': 'Goodbrand H. B.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Goodbrand H. B.10.1021/ja00381a024
10.1002/jlac.198619860410
10.1021/jo00229a024
10.1016/S0040-4039(00)84231-8
{'key': 'e_1_2_1_524_2', 'first-page': '519', 'volume': '957', 'author': 'Pearson A. J.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Pearson A. J.{'key': 'e_1_2_1_525_2', 'first-page': '1523', 'volume': '1986', 'author': 'Breitgoff D.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Breitgoff D.10.1021/jo00248a046
10.1016/S0040-4039(00)96663-2
10.1021/ja00399a043
10.1016/S0040-4039(00)99101-9
10.1002/jlac.199019900172
10.1002/nadc.19860341006
10.1002/cber.19811140811
10.1016/S0040-4039(00)81829-8
10.1071/CH9762459
10.1002/hlca.19890720410
10.1002/hlca.19870700618
- …. or might one here employ the adjectivepromiscuous?Cf. the classical picture of the “key and keyhole”.
10.1021/ja00538a077
10.1021/ja00410a053
{'key': 'e_1_2_1_537_4', 'first-page': '194', 'volume-title': 'Asymmetric Synthesis', 'author': 'Rossiter B. E.', 'year': '1985'}
/ Asymmetric Synthesis by Rossiter B. E. (1985)- “Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Epoxidation”;
10.1055/s-1986-31489
10.1002/nadc.19890371210
10.1021/jo00360a058
10.1021/ja00230a045
10.1021/jo00293a001
- This has been designated us “reagent control” [437]—in contrast to “substrate control”. In German it would have to be expressed as “durch das Reagens gesteuert”. I well remember the sermons on a similar theme by my thesis advisorRudolf Criegee who was at that time editor of “Chemische Berichte:es muß heißen kinetisch oder thermodynamichgesteuerte.nicht kontrollierte Reaktion; Kontrolle hat im Deutschen cine vom Englischen ‘control’ verschiedene Bedeutung!” From the fact that the term “stereocontrol” is about to replace “stereoselectivity” we must conclude that now everything is “under control”.
- “Asymmetric Synthesis using Organometallic Catalysts”:H. B.Kaganin [388] Vol. 8 chap. 53. pp. 463–498 and the original literature cited therein.
10.1016/B978-0-08-092493-9.50011-6
10.1002/ange.19870990304
10.1002/anie.198701901
10.1021/cr00098a001
10.1021/ja00188a089
10.1021/jo00230a017
10.1021/ja00365a030
10.1021/jo00211a039
10.1016/S0040-4039(00)98780-X
10.1021/ja00214a053
10.1021/ja00280a056
10.1016/S0040-4039(00)82336-9
10.1021/ja00196a045
{'key': 'e_1_2_1_547_2', 'first-page': '1', 'volume-title': 'Organic Synthesis‐Theory and Applications, A Research Annual', 'author': 'Taschner M. J.', 'year': '1989'}
/ Organic Synthesis‐Theory and Applications, A Research Annual by Taschner M. J. (1989)10.1002/nadc.19870350307
- see also the article byHelmchenet al. [462]:
10.1021/jo00268a001
10.1021/ja00187a093
- One should also note that it has become common to speak of Lewis acid‐catalyzed reactions even when equimolar amounts or even lame excesses of SnCl4. TiX4. or BF3—ether are added in which case the Lewis acid could be regarded as part of the solvent!
10.1016/B978-0-08-092493-9.50007-4
- See for example the semicorrin ligand proposed for transition‐metal‐catalyzed reactions byA. Pfaltz[490e] as well as B and C in Scheme 32.
10.1021/ja00279a083
10.1016/S0040-4039(00)96695-4
10.1021/jo00290a002
10.1016/S0040-4039(00)99546-7
10.1021/ja00248a045
{'key': 'e_1_2_1_553_3', 'first-page': '1302', 'volume': '1987', 'author': 'Yamada J.', 'journal-title': 'J. Chem. Soc. Chem. Commun.'}
/ J. Chem. Soc. Chem. Commun. by Yamada J.10.5059/yukigoseikyokaishi.45.101
- With few exceptions lithium also docs not exceed the limit of four tetrahedrally oriented ligands; sec (172) and references cited therein. Higher coordination numbers with this element appear to result largely from ionic interactions.
- Mean lengths for the bonds [Å] between N C and O and a number of the metals that are important in synthetic applications.Commentary: The average bond length for pure B/C/N/O‐compounds are taken from [102a]. Average bond lengths for Ti and Zn compounds are derived from [102h] and apply to compounds containing a metal bonded to a methyl group or complexes with aliphatic amines or aliphatic ethers. In the case of the Ti‐CH3 group only two widely divergent values have been reported (1.969 and 2.206 Å). The rest of the data resulted from a search in the CSD [189] for comparable bonds (only trimethyl compounds in the case of Al‐C and Sn‐C). If more than twenty values were found the average has been supplemented (in parentheses) with the standard deviation applicable to the last reported digit. Since the reported values were obtained on the basis of differing criteria they should be regarded only as points of reference.
10.1021/ja00187a061
{'key': 'e_1_2_1_557_3', 'first-page': '49', 'volume-title': 'Stere‐ochemistry of Organic and Bioorganic Transformations, Workshop Conferences Hoechst', 'author': 'Masamune S.', 'year': '1987'}
/ Stere‐ochemistry of Organic and Bioorganic Transformations, Workshop Conferences Hoechst by Masamune S. (1987)- E. J.Corey Proc. 31st Natl. Org. Symp. Am. Chem. Soc.June 1989 pp. 1–14
10.1021/ja00252a056
10.1021/ja00259a075
10.1016/S0040-4039(01)93796-7
10.1016/S0040-4039(00)94578-7
10.1021/jo00247a044
10.1016/S0040-4039(00)94581-7
10.1016/S0040-4039(00)82359-X
10.1021/ja00219a059
10.1016/0040-4039(88)85121-9
10.1016/S0040-4039(01)93871-7
10.1002/hlca.19770600202
- The prophetic observations ofWoodwardin his famous 1956 essay on the subject of “Synthesis” [39] remain just as valid today. On the other hand it was left to a magician like Stork to propose a time scale: “So it is not surprising that organic synthesis is far from the level that many people assume. Progress is continuing hut there will not be any dramatic developments. It is more like a glacier that gradually moves forward until it has finally covered an entire region but it will still becenturiesbefore synthesis has acquired the status that many people already ascribe to it today” [44].
Dates
Type | When |
---|---|
Created | 21 years, 8 months ago (Dec. 31, 2003, 4:03 a.m.) |
Deposited | 1 year, 7 months ago (Jan. 11, 2024, 3:23 p.m.) |
Indexed | 2 days, 16 hours ago (Sept. 3, 2025, 5:50 a.m.) |
Issued | 34 years, 10 months ago (Nov. 1, 1990) |
Published | 34 years, 10 months ago (Nov. 1, 1990) |
Published Online | 21 years, 8 months ago (Dec. 22, 2003) |
Published Print | 34 years, 10 months ago (Nov. 1, 1990) |
@article{Seebach_1990, title={Organic Synthesis—Where now?}, volume={29}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199013201}, DOI={10.1002/anie.199013201}, number={11}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Seebach, Dieter}, year={1990}, month=nov, pages={1320–1367} }