DOI: 10.1002/ange.200704972. Tripeptides as Efficient Asymmetric Catalysts for 1,4‐Addition Reactions of Aldehydes to Nitroolefins

Tripeptides as Efficient Asymmetric Catalysts for 1,4‐Addition Reactions of Aldehydes to Nitroolefins–A Rational Approach

10.1002/ange.200704972

Crossref journal-article

Wiley

Angewandte Chemie (311)

Bibliography

Wiesner, M., Revell, J. D., & Wennemers, H. (2008). Tripeptides as Efficient Asymmetric Catalysts for 1,4âAddition Reactions of Aldehydes to NitroolefinsâA Rational Approach. Angewandte Chemie, 120(10), 1897â1900. Portico.

Authors 3

Markus Wiesner (first)
Jefferson D. Revell (additional)
Helma Wennemers (additional)

References 82 Referenced 90

For reviews see:
10.1016/j.cbpa.2007.05.015
10.2174/1570178053765285
10.1021/ar030061c
For reviews see:
10.1007/128_2007_117
10.1016/j.cbpa.2004.04.013
10.1016/S1367-5931(03)00065-6
10.1021/ol0500259
10.1002/bip.20393
10.1016/j.tet.2007.06.010
10.1002/ange.200460916
10.1002/anie.200460916
10.1073/pnas.0307979101
10.1021/ja028812d
10.1021/ja028634o
10.1002/1099-0690(200206)2002:12<1877::AID-EJOC1877>3.0.CO;2-U
For recent reviews on 1 4‐addition reactions catalyzed by organocatalysts see:
10.1002/ejoc.200600653
10.1039/b701216k
10.1055/s-2007-983747
10.1016/j.tetasy.2007.01.023
For examples of peptides catalyzing conjugate addition reactions see:
10.1016/j.tetasy.2006.03.012
10.1039/B514783M
10.1002/adsc.200505373
10.1055/s-2004-834830
10.1002/ejoc.200400243
{'key': 'e_1_2_3_30_2', 'first-page': '1901', 'author': 'Martin H. J.', 'year': '2003', 'journal-title': 'Synlett'} / Synlett by Martin H. J. (2003)
10.1021/ja0177814
10.1002/1521-3757(20001016)112:20<3781::AID-ANGE3781>3.0.CO;2-H
10.1002/1521-3773(20001016)39:20<3635::AID-ANIE3635>3.0.CO;2-Y
For additions of carbonyl compounds to nitroolefins catalyzed by proline see:
10.1080/00397910600978218
10.1002/ejoc.200300648
10.1055/s-2002-19336
10.1021/ja010037z
10.1021/ol015799d
For examples of conjugate additions between aldehydes and nitroolefins catalyzed by organocatalysts see:
10.1021/ol0628006
10.1021/ol071366k
10.1021/ol7015498
{'key': 'e_1_2_3_43_2', 'first-page': '737', 'author': 'Ni B.', 'year': '2007', 'journal-title': 'Chem. Commun.'} / Chem. Commun. by Ni B. (2007)
10.1002/ejoc.200600731
10.1021/ja0620890
10.1002/ange.200602221
10.1002/anie.200602221
10.1016/j.tetasy.2006.07.004
10.1021/ol060481c
10.1002/ange.200602207
10.1002/anie.200602207
10.1021/ol0614727
10.1021/ol0607490
10.1021/ja060338e
10.1002/chem.200600115
10.1021/ol061053
10.1016/j.tetlet.2006.05.067
10.1002/ange.200600048
10.1002/anie.200600048
10.1038/nature04820
{'key': 'e_1_2_3_58_2', 'first-page': '611', 'author': 'Mitchell C. E. T.', 'year': '2005', 'journal-title': 'Synlett'} / Synlett by Mitchell C. E. T. (2005)
10.1002/ange.200500599
10.1002/anie.200500599
10.1002/ange.200461959
10.1002/anie.200461959
10.1021/ja046871g
10.1002/adsc.200404037
10.1021/ol049196o
10.1021/ol026543q
10.1021/ol0167006
Experiments with peptides bearing a protected secondary amine or a protected carboxylic acid were either not catalytically active or showed significantly poorer catalytic properties; see theSupporting Information.
For an organocatalytic route to β2‐amino acids see:
10.1021/ja070063i
10.1021/ja061731n
For examples of the use of 5 mol % of catalyst and efficient catalysis with aliphatic aldehydes see reference [10].
Peptides1and4can be easily prepared on a 10‐g scale within a day by standard solid‐phase synthesis using the Fmoc/tBu protocol for peptide synthesis.
10.1002/jcc.540110405
10.1021/ja9621760
Molecular modelling studies with peptides2and3revealed lowest energy conformations similar to that of peptide1 thereby accounting for their respective stereoselectivities see theSupporting Information.
10.1002/anie.200704161

Dates

Type	When
Created	17 years, 7 months ago (Jan. 28, 2008, 1:51 p.m.)
Deposited	1 year, 10 months ago (Oct. 17, 2023, 1:27 a.m.)
Indexed	1 year, 4 months ago (April 15, 2024, 5:05 a.m.)
Issued	17 years, 6 months ago (Feb. 15, 2008)
Published	17 years, 6 months ago (Feb. 15, 2008)
Published Online	17 years, 6 months ago (Feb. 15, 2008)
Published Print	17 years, 6 months ago (Feb. 22, 2008)

Funders 0

None

BibTeX

@article{Wiesner_2008, title={Tripeptides as Efficient Asymmetric Catalysts for 1,4‐Addition Reactions of Aldehydes to Nitroolefins–A Rational Approach}, volume={120}, ISSN={1521-3757}, url={http://dx.doi.org/10.1002/ange.200704972}, DOI={10.1002/ange.200704972}, number={10}, journal={Angewandte Chemie}, publisher={Wiley}, author={Wiesner, Markus and Revell, Jefferson D. and Wennemers, Helma}, year={2008}, month=feb, pages={1897–1900} }

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    "10.1002/ange.200704972"
  ],
  "URL": "http://dx.doi.org/10.1002/ange.200704972",
  "relation": {},
  "ISSN": [
    "0044-8249",
    "1521-3757"
  ],
  "subject": [],
  "container-title-short": "Angewandte Chemie",
  "published": {
    "date-parts": [
      [
        2008,
        2,
        15
      ]
    ]
  }
}