DOI: 10.1002/anie.200600327. Highly Enantioselective Aza‐Baylis–Hillman Reaction in a Chiral Reaction Medium

Highly Enantioselective Aza‐Baylis–Hillman Reaction in a Chiral Reaction Medium

10.1002/anie.200600327

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Gausepohl, R., Buskens, P., Kleinen, J., Bruckmann, A., Lehmann, C. W., Klankermayer, J., & Leitner, W. (2006). Highly Enantioselective AzaâBaylisâHillman Reaction in a Chiral Reaction Medium. Angewandte Chemie International Edition, 45(22), 3689â3692. Portico.

Authors 7

Rolf Gausepohl (first)
Pascal Buskens (additional)
Jochen Kleinen (additional)
Angelika Bruckmann (additional)
Christian W. Lehmann (additional)
Jürgen Klankermayer (additional)
Walter Leitner (additional)

References 37 Referenced 164

{'key': 'e_1_2_4_1_2', 'volume-title': 'Compendium of Chiral Auxiliary Applications', 'author': 'Roos G. H.', 'year': '2001'} / Compendium of Chiral Auxiliary Applications by Roos G. H. (2001)
10.1007/978-3-642-58571-5
10.1002/3527604677
{'key': 'e_1_2_4_5_2', 'volume-title': 'Solvents and Solvent Effects in Organic Chemistry', 'author': 'Reichardt C.', 'year': '2003'} / Solvents and Solvent Effects in Organic Chemistry by Reichardt C. (2003)
10.1021/cr010043d
10.1016/j.tet.2005.01.130
10.1002/1521-3757(20021202)114:23<4689::AID-ANGE4689>3.0.CO;2-2
10.1002/1521-3773(20021202)41:23<4507::AID-ANIE4507>3.0.CO;2-I
10.1016/S0040-4039(03)00289-2
10.1039/B301863F
10.1021/ja0447255
10.1021/ja0500254
10.1002/ange.19750871709
10.1002/anie.197506341
10.1002/1521-3757(20001103)112:21<3926::AID-ANGE3926>3.0.CO;2-U
10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
{'key': 'e_1_2_4_17_2', 'volume-title': 'Ionic Liquids in Synthesis', 'author': 'Wasserscheid P.', 'year': '2003'} / Ionic Liquids in Synthesis by Wasserscheid P. (2003)
For recent reviews on chiral ILs see:
10.1016/j.tetasy.2005.10.026
10.1002/chir.20153
10.1016/j.tetlet.2004.06.134
10.1021/ol047599i
10.1016/j.tetlet.2005.04.134
10.1021/ja0550024
The corresponding Li salt:P. H.Cunningham F. L.Warren Jr. H. O.Marcy M. J.Rosker(Rockwell International Corp. USA) EP‐95‐109113 693704 1996.
Crystal data for8: C8H8BNaO10 Mr=297.9 crystal dimensions 0.36×0.34×0.25 mm3 monoclinicP21(No. 4) T=100 Ka=5.40160(10) b=11.6781(2) c=9.4451(2) Å β=105.0590(10) V=575.340(19) Å3 ρcalcd=1.720 Mg m−3 CuKαradiation λ=1.54178 Å. CCD scans yielded 10 760 (1906 unique) reflections Rint=0.038. Multi‐scan absorption correction μ=1.719 mm−1 Tmin=0.85 Tmax=1.0. Structure solution (direct methods) SHELXS‐97 full‐matrix least‐squares refinement against F2SHELXL‐97 213 parameters hydrogen atoms in idealized geometry (riding model) R=0.025 wR=0.077 highest residual electron density peak 0.2 Å−3. Complete lists of atom coordinates and anisotropic displacement parameters as well as tables of bond lengths and bond angles are available as supplementary material. CCDC‐297143 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
10.1002/recl.19250440903
10.1039/b005954o
10.1039/b205251m
The melting point was determined by differential scanning calorimetry; 72±2 % conversion (determined from1H NMR spectroscopy); impurities: octanol (from aliquat 336 up to 6 %) water (200–2800 ppm determined by Karl Fischer titration).
The absolute configuration of4 a–cwas assigned asRby comparison with the work of Shi et al.[6d]
The possibility of enrichment of one enantiomer during workup was excluded by subjecting a scalemic mixture of4 cto the same experimental procedure. This control material had 74 %ee(S) before and 76 %ee(S) after the workup procedure.

Dates

Type	When
Created	19 years, 3 months ago (May 18, 2006, 6:35 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 4:58 p.m.)
Indexed	1 year, 2 months ago (July 2, 2024, 3:11 p.m.)
Issued	19 years, 3 months ago (May 18, 2006)
Published	19 years, 3 months ago (May 18, 2006)
Published Online	19 years, 3 months ago (May 18, 2006)
Published Print	19 years, 3 months ago (May 26, 2006)

Funders 0

None

BibTeX

@article{Gausepohl_2006, title={Highly Enantioselective Aza‐Baylis–Hillman Reaction in a Chiral Reaction Medium}, volume={45}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200600327}, DOI={10.1002/anie.200600327}, number={22}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Gausepohl, Rolf and Buskens, Pascal and Kleinen, Jochen and Bruckmann, Angelika and Lehmann, Christian W. and Klankermayer, Jürgen and Leitner, Walter}, year={2006}, month=may, pages={3689–3692} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        7,
        2
      ]
    ],
    "date-time": "2024-07-02T19:11:55Z",
    "timestamp": 1719947515849
  },
  "reference-count": 37,
  "publisher": "Wiley",
  "issue": "22",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2006,
            5,
            18
          ]
        ],
        "date-time": "2006-05-18T00:00:00Z",
        "timestamp": 1147910400000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2006,
        5,
        26
      ]
    ]
  },
  "DOI": "10.1002/anie.200600327",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        5,
        18
      ]
    ],
    "date-time": "2006-05-18T10:35:20Z",
    "timestamp": 1147948520000
  },
  "page": "3689-3692",
  "source": "Crossref",
  "is-referenced-by-count": 164,
  "title": "Highly Enantioselective Aza\u2010Baylis\u2013Hillman Reaction in a Chiral Reaction Medium",
  "prefix": "10.1002",
  "volume": "45",
  "author": [
    {
      "given": "Rolf",
      "family": "Gausepohl",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Pascal",
      "family": "Buskens",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Jochen",
      "family": "Kleinen",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Angelika",
      "family": "Bruckmann",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Christian W.",
      "family": "Lehmann",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "J\u00fcrgen",
      "family": "Klankermayer",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Walter",
      "family": "Leitner",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2006,
        5,
        18
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_4_1_2",
      "volume-title": "Compendium of Chiral Auxiliary Applications",
      "author": "Roos G. H.",
      "year": "2001"
    },
    {
      "key": "e_1_2_4_2_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_4_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-3-642-58571-5"
    },
    {
      "key": "e_1_2_4_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/3527604677"
    },
    {
      "key": "e_1_2_4_5_2",
      "volume-title": "Solvents and Solvent Effects in Organic Chemistry",
      "author": "Reichardt C.",
      "year": "2003"
    },
    {
      "key": "e_1_2_4_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr010043d"
    },
    {
      "key": "e_1_2_4_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.tet.2005.01.130"
    },
    {
      "key": "e_1_2_4_8_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_4_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1521-3757(20021202)114:23<4689::AID-ANGE4689>3.0.CO;2-2"
    },
    {
      "key": "e_1_2_4_9_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1521-3773(20021202)41:23<4507::AID-ANIE4507>3.0.CO;2-I"
    },
    {
      "key": "e_1_2_4_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(03)00289-2"
    },
    {
      "key": "e_1_2_4_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/B301863F"
    },
    {
      "key": "e_1_2_4_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0447255"
    },
    {
      "key": "e_1_2_4_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0500254"
    },
    {
      "key": "e_1_2_4_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19750871709"
    },
    {
      "key": "e_1_2_4_14_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.197506341"
    },
    {
      "key": "e_1_2_4_15_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_4_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1521-3757(20001103)112:21<3926::AID-ANGE3926>3.0.CO;2-U"
    },
    {
      "key": "e_1_2_4_16_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5"
    },
    {
      "key": "e_1_2_4_17_2",
      "volume-title": "Ionic Liquids in Synthesis",
      "author": "Wasserscheid P.",
      "year": "2003"
    },
    {
      "key": "e_1_2_4_18_2",
      "unstructured": "For recent reviews on chiral ILs see:"
    },
    {
      "key": "e_1_2_4_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.tetasy.2005.10.026"
    },
    {
      "key": "e_1_2_4_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/chir.20153"
    },
    {
      "key": "e_1_2_4_21_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_4_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.tetlet.2004.06.134"
    },
    {
      "key": "e_1_2_4_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ol047599i"
    },
    {
      "key": "e_1_2_4_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.tetlet.2005.04.134"
    },
    {
      "key": "e_1_2_4_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0550024"
    },
    {
      "key": "e_1_2_4_26_2",
      "unstructured": "The corresponding Li salt:P. H.Cunningham F. L.Warren Jr. H. O.Marcy M. J.Rosker(Rockwell International Corp. USA) EP\u201095\u2010109113 693704 1996."
    },
    {
      "key": "e_1_2_4_27_2",
      "unstructured": "Crystal data for8: C8H8BNaO10 Mr=297.9 crystal dimensions 0.36\u00d70.34\u00d70.25 mm3 monoclinicP21(No. 4) T=100 Ka=5.40160(10) b=11.6781(2) c=9.4451(2) \u00c5 \u03b2=105.0590(10) V=575.340(19) \u00c53 \u03c1calcd=1.720 Mg\u2009m\u22123 CuK\u03b1radiation \u03bb=1.54178 \u00c5. CCD scans yielded 10\u2009760 (1906 unique) reflections Rint=0.038. Multi\u2010scan absorption correction \u03bc=1.719 mm\u22121 Tmin=0.85 Tmax=1.0. Structure solution (direct methods) SHELXS\u201097 full\u2010matrix least\u2010squares refinement against F2SHELXL\u201097 213 parameters hydrogen atoms in idealized geometry (riding model) R=0.025 wR=0.077 highest residual electron density peak 0.2 \u00c5\u22123. Complete lists of atom coordinates and anisotropic displacement parameters as well as tables of bond lengths and bond angles are available as supplementary material. CCDC\u2010297143 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif."
    },
    {
      "key": "e_1_2_4_28_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_4_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/recl.19250440903"
    },
    {
      "key": "e_1_2_4_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b005954o"
    },
    {
      "key": "e_1_2_4_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b205251m"
    },
    {
      "key": "e_1_2_4_32_2",
      "unstructured": "The melting point was determined by differential scanning calorimetry; 72\u00b12\u2009% conversion (determined from1H NMR spectroscopy); impurities: octanol (from aliquat 336 up to 6\u2009%) water (200\u20132800 ppm determined by Karl Fischer titration)."
    },
    {
      "key": "e_1_2_4_33_2",
      "unstructured": "The absolute configuration of4\u2009a\u2013cwas assigned asRby comparison with the work of Shi et al.[6d]"
    },
    {
      "key": "e_1_2_4_34_2",
      "unstructured": "The possibility of enrichment of one enantiomer during workup was excluded by subjecting a scalemic mixture of4\u2009cto the same experimental procedure. This control material had 74\u2009%ee(S) before and 76\u2009%ee(S) after the workup procedure."
    }
  ],
  "container-title": "Angewandte Chemie International Edition",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.200600327",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.200600327",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        16
      ]
    ],
    "date-time": "2023-10-16T20:58:27Z",
    "timestamp": 1697489907000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.200600327"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2006,
        5,
        18
      ]
    ]
  },
  "references-count": 37,
  "journal-issue": {
    "issue": "22",
    "published-print": {
      "date-parts": [
        [
          2006,
          5,
          26
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.200600327"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.200600327",
  "relation": {},
  "ISSN": [
    "1433-7851",
    "1521-3773"
  ],
  "subject": [],
  "container-title-short": "Angew Chem Int Ed",
  "published": {
    "date-parts": [
      [
        2006,
        5,
        18
      ]
    ]
  }
}