DOI: 10.1021/ja028812d. Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions

Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions

10.1021/ja028812d

Crossref journal-article

American Chemical Society (ACS)

Journal of the American Chemical Society (316)

Bibliography

Bahmanyar, S., Houk, K. N., Martin, H. J., & List, B. (2003). Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions. Journal of the American Chemical Society, 125(9), 2475â2479.

Authors 4

S. Bahmanyar (first)
K. N. Houk (additional)
Harry J. Martin (additional)
Benjamin List (additional)

References 32 Referenced 546

{'key': 'ja028812db00001/ja028812db00001_1', 'first-page': '733', 'volume': '123', 'author': 'Dirac P. A. M.', 'year': '1929', 'journal-title': 'Proc. R. Soc.'} / Proc. R. Soc. by Dirac P. A. M. (1929)
{'key': 'ja028812db00002/ja028812db00002_1', 'first-page': '662', 'volume': '54', 'author': 'Gill P. M. W.', 'year': '2001', 'journal-title': 'Aust. J. Chem.'} / Aust. J. Chem. by Gill P. M. W. (2001)
{'key': 'ja028812db00003/ja028812db00003_1', 'first-page': '3243', 'volume': '38', 'author': 'Hajos Z. G.', 'year': '1973', 'journal-title': 'J. Org. Chem.'} / J. Org. Chem. by Hajos Z. G. (1973)
{'key': 'ja028812db00003/ja028812db00003_2', 'first-page': '1621', 'volume': '39', 'author': 'Hajos Z. G.', 'year': '1974', 'journal-title': 'J. Org. Chem.'} / J. Org. Chem. by Hajos Z. G. (1974)
10.1002/anie.197104961 / Angew. Chem., Int. Ed. Engl. by Eder U. (1971)
{'key': 'ja028812db00003/ja028812db00003_4', 'first-page': '1109', 'volume': '23', 'author': 'Experiments', 'year': '1975', 'journal-title': 'Chem. Pharm. Bull.'} / Chem. Pharm. Bull. by Experiments (1975)
10.1016/S0040-4020(02)00516-1 / Tetrahedron by List B. (2002)
{'key': 'ja028812db00004/ja028812db00004_1', 'first-page': '2396', 'volume': '122', 'author': 'List B.', 'year': '2000', 'journal-title': 'III J. Am. Chem. Soc.'} / III J. Am. Chem. Soc. by List B. (2000)
10.1021/ja001460v / J. Am. Chem. Soc. by Notz W. (2000)
{'key': 'ja028812db00006/ja028812db00006_1', 'first-page': '575', 'volume': '3', 'author': 'List B.', 'year': '2001', 'journal-title': 'Org. Lett.'} / Org. Lett. by List B. (2001)
{'key': 'ja028812db00007/ja028812db00007_1', 'first-page': '1686', 'volume': '11', 'author': 'List B.', 'year': '2001', 'journal-title': 'Synlett'} / Synlett by List B. (2001)
{'key': 'ja028812db00008/ja028812db00008_1', 'first-page': '5267', 'volume': '123', 'author': 'Sakthivel K.', 'year': '2001', 'journal-title': 'III J. Am. Chem. Soc.'} / III J. Am. Chem. Soc. by Sakthivel K. (2001)
{'key': 'ja028812db00009/ja028812db00009_1', 'first-page': '303', 'volume': '67', 'author': 'Côrdova A.', 'year': '2002', 'journal-title': 'III J. Org. Chem.'} / III J. Org. Chem. by Côrdova A. (2002)
{'key': 'ja028812db00010/ja028812db00010_1', 'first-page': '3135', 'volume': '298', 'author': 'Brown K. L.', 'year': '1978', 'journal-title': 'Helv. Chim. Acta'} / Helv. Chim. Acta by Brown K. L. (1978)
{'key': 'ja028812db00010/ja028812db00010_2', 'first-page': '31', 'volume': '32', 'author': 'Jung M. E.', 'year': '1976', 'journal-title': 'Tetrahedron'} / Tetrahedron by Jung M. E. (1976)
{'key': 'ja028812db00011/ja028812db00011_1', 'first-page': '507', 'volume': '3', 'author': 'Agami C.', 'year': '1988', 'journal-title': 'Bull. Soc. Chim. Fr.'} / Bull. Soc. Chim. Fr. by Agami C. (1988)
{'key': 'ja028812db00012/ja028812db00012_1', 'first-page': '360', 'volume': '2', 'author': 'Agami C.', 'year': '1987', 'journal-title': 'Bull. Soc. Chim. Fr.'} / Bull. Soc. Chim. Fr. by Agami C. (1987)
10.1002/1521-3773(20010202)40:3<529::AID-ANIE529>3.0.CO;2-X / Angew. Chem., Int. Ed. by Gröger H. (2001)
10.1016/S0040-4020(02)00122-9 / J. Tetrahedron by Jarvo E. R. (2002)
{'key': 'ja028812db00014/ja028812db00014_1', 'first-page': '6799', 'volume': '124', 'author': 'MacMillan D. W. C.', 'year': '2002', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by MacMillan D. W. C. (2002)
{'key': 'ja028812db00015/ja028812db00015_1', 'first-page': '1923', 'volume': '79', 'author': 'Zimmerman H. E.', 'year': '1957', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Zimmerman H. E. (1957)
{'key': 'ja028812db00016/ja028812db00016_1', 'first-page': '12912', 'volume': '123', 'author': 'Bahmanyar S.', 'year': '2001', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Bahmanyar S. (2001)
{'key': 'ja028812db00017/ja028812db00017_1', 'first-page': '283', 'volume': '123', 'author': 'Bahmanyar S.', 'year': '2001', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Bahmanyar S. (2001)
{'key': 'ja028812db00018/ja028812db00018_1', 'first-page': '1377', 'volume': '98', 'author': 'Becke A. D.', 'year': '1993', 'journal-title': 'J. Chem. Phys.'} / J. Chem. Phys. by Becke A. D. (1993)
{'key': 'ja028812db00018/ja028812db00018_2', 'first-page': '789', 'volume': '37', 'author': 'Lee C.', 'year': '1988', 'journal-title': 'Phys. Rev. B'} / Phys. Rev. B by Lee C. (1988)
{'key': 'ja028812db00019/ja028812db00019_1', 'first-page': '728', 'volume': '54', 'author': 'Ditchfield R.', 'year': '1971', 'journal-title': 'J. Chem. Phys.'} / J. Chem. Phys. by Ditchfield R. (1971)
{'key': 'ja028812db00019/ja028812db00019_2', 'first-page': '2261', 'volume': '56', 'author': 'Hehre W. J.', 'year': '1972', 'journal-title': 'J. Chem. Phys.'} / J. Chem. Phys. by Hehre W. J. (1972)
10.1007/BF00533485 / Theor. Chim. Acta by Hariharan P. C. (1973)
{'key': 'ja028812db00020/ja028812db00020_1', 'volume-title': 'Gaussian', 'author': 'Frisch M. J.', 'year': '1998'} / Gaussian by Frisch M. J. (1998)
10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W / J. Comput. Chem. by Barone B. (1998)
{'key': 'ja028812db00022/ja028812db00022_1', 'volume': '106', 'author': 'After', 'year': '2002', 'journal-title': 'J. Phys. Chem. A.'} / J. Phys. Chem. A. by After (2002)
{'key': 'ja028812db00023/ja028812db00023_1', 'first-page': '7169', 'volume': '124', 'author': 'These', 'year': '2002', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by These (2002)

Dates

Type	When
Created	22 years, 6 months ago (Feb. 26, 2003, 2:11 a.m.)
Deposited	3 years, 10 months ago (Oct. 5, 2021, 7:53 a.m.)
Indexed	1 week, 1 day ago (Aug. 21, 2025, 12:58 p.m.)
Issued	22 years, 6 months ago (Feb. 8, 2003)
Published	22 years, 6 months ago (Feb. 8, 2003)
Published Online	22 years, 6 months ago (Feb. 8, 2003)
Published Print	22 years, 5 months ago (March 1, 2003)

Funders 0

None

BibTeX

@article{Bahmanyar_2003, title={Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions}, volume={125}, ISSN={1520-5126}, url={http://dx.doi.org/10.1021/ja028812d}, DOI={10.1021/ja028812d}, number={9}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Bahmanyar, S. and Houk, K. N. and Martin, Harry J. and List, Benjamin}, year={2003}, month=feb, pages={2475–2479} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        21
      ]
    ],
    "date-time": "2025-08-21T16:58:06Z",
    "timestamp": 1755795486586
  },
  "reference-count": 32,
  "publisher": "American Chemical Society (ACS)",
  "issue": "9",
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2003,
        3,
        1
      ]
    ]
  },
  "DOI": "10.1021/ja028812d",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        2,
        26
      ]
    ],
    "date-time": "2003-02-26T07:11:35Z",
    "timestamp": 1046243495000
  },
  "page": "2475-2479",
  "source": "Crossref",
  "is-referenced-by-count": 546,
  "title": "Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions",
  "prefix": "10.1021",
  "volume": "125",
  "author": [
    {
      "given": "S.",
      "family": "Bahmanyar",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037"
        }
      ]
    },
    {
      "given": "K. N.",
      "family": "Houk",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037"
        }
      ]
    },
    {
      "given": "Harry J.",
      "family": "Martin",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037"
        }
      ]
    },
    {
      "given": "Benjamin",
      "family": "List",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Contribution from the Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037"
        }
      ]
    }
  ],
  "member": "316",
  "published-online": {
    "date-parts": [
      [
        2003,
        2,
        8
      ]
    ]
  },
  "reference": [
    {
      "key": "ja028812db00001/ja028812db00001_1",
      "first-page": "733",
      "volume": "123",
      "author": "Dirac P. A. M.",
      "year": "1929",
      "journal-title": "Proc. R. Soc."
    },
    {
      "key": "ja028812db00002/ja028812db00002_1",
      "first-page": "662",
      "volume": "54",
      "author": "Gill P. M. W.",
      "year": "2001",
      "journal-title": "Aust. J. Chem."
    },
    {
      "key": "ja028812db00003/ja028812db00003_1",
      "first-page": "3243",
      "volume": "38",
      "author": "Hajos Z. G.",
      "year": "1973",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "ja028812db00003/ja028812db00003_2",
      "first-page": "1621",
      "volume": "39",
      "author": "Hajos Z. G.",
      "year": "1974",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "ja028812db00003/ja028812db00003_3",
      "doi-asserted-by": "crossref",
      "first-page": "497",
      "DOI": "10.1002/anie.197104961",
      "volume": "10",
      "author": "Eder U.",
      "year": "1971",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "ja028812db00003/ja028812db00003_4",
      "first-page": "1109",
      "volume": "23",
      "author": "Experiments",
      "year": "1975",
      "journal-title": "Chem. Pharm. Bull."
    },
    {
      "key": "ja028812db00003/ja028812db00003_5",
      "doi-asserted-by": "crossref",
      "first-page": "5590",
      "DOI": "10.1016/S0040-4020(02)00516-1",
      "volume": "58",
      "author": "List B.",
      "year": "2002",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "ja028812db00004/ja028812db00004_1",
      "first-page": "2396",
      "volume": "122",
      "author": "List B.",
      "year": "2000",
      "journal-title": "III J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00005/ja028812db00005_1",
      "doi-asserted-by": "crossref",
      "first-page": "7387",
      "DOI": "10.1021/ja001460v",
      "volume": "122",
      "author": "Notz W.",
      "year": "2000",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00006/ja028812db00006_1",
      "first-page": "575",
      "volume": "3",
      "author": "List B.",
      "year": "2001",
      "journal-title": "Org. Lett."
    },
    {
      "key": "ja028812db00007/ja028812db00007_1",
      "first-page": "1686",
      "volume": "11",
      "author": "List B.",
      "year": "2001",
      "journal-title": "Synlett"
    },
    {
      "key": "ja028812db00008/ja028812db00008_1",
      "first-page": "5267",
      "volume": "123",
      "author": "Sakthivel K.",
      "year": "2001",
      "journal-title": "III J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00009/ja028812db00009_1",
      "first-page": "303",
      "volume": "67",
      "author": "C\u00f4rdova A.",
      "year": "2002",
      "journal-title": "III J. Org. Chem."
    },
    {
      "key": "ja028812db00010/ja028812db00010_1",
      "first-page": "3135",
      "volume": "298",
      "author": "Brown K. L.",
      "year": "1978",
      "journal-title": "Helv. Chim. Acta"
    },
    {
      "key": "ja028812db00010/ja028812db00010_2",
      "first-page": "31",
      "volume": "32",
      "author": "Jung M. E.",
      "year": "1976",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "ja028812db00011/ja028812db00011_1",
      "first-page": "507",
      "volume": "3",
      "author": "Agami C.",
      "year": "1988",
      "journal-title": "Bull. Soc. Chim. Fr."
    },
    {
      "key": "ja028812db00012/ja028812db00012_1",
      "first-page": "360",
      "volume": "2",
      "author": "Agami C.",
      "year": "1987",
      "journal-title": "Bull. Soc. Chim. Fr."
    },
    {
      "key": "ja028812db00013/ja028812db00013_1",
      "doi-asserted-by": "crossref",
      "first-page": "532",
      "DOI": "10.1002/1521-3773(20010202)40:3<529::AID-ANIE529>3.0.CO;2-X",
      "volume": "40",
      "author": "Gr\u00f6ger H.",
      "year": "2001",
      "journal-title": "Angew. Chem., Int. Ed."
    },
    {
      "key": "ja028812db00013/ja028812db00013_2",
      "doi-asserted-by": "crossref",
      "first-page": "2495",
      "DOI": "10.1016/S0040-4020(02)00122-9",
      "volume": "58",
      "author": "Jarvo E. R.",
      "year": "2002",
      "journal-title": "J. Tetrahedron"
    },
    {
      "key": "ja028812db00014/ja028812db00014_1",
      "first-page": "6799",
      "volume": "124",
      "author": "MacMillan D. W. C.",
      "year": "2002",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00015/ja028812db00015_1",
      "first-page": "1923",
      "volume": "79",
      "author": "Zimmerman H. E.",
      "year": "1957",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00016/ja028812db00016_1",
      "first-page": "12912",
      "volume": "123",
      "author": "Bahmanyar S.",
      "year": "2001",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00017/ja028812db00017_1",
      "first-page": "283",
      "volume": "123",
      "author": "Bahmanyar S.",
      "year": "2001",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja028812db00018/ja028812db00018_1",
      "first-page": "1377",
      "volume": "98",
      "author": "Becke A. D.",
      "year": "1993",
      "journal-title": "J. Chem. Phys."
    },
    {
      "key": "ja028812db00018/ja028812db00018_2",
      "first-page": "789",
      "volume": "37",
      "author": "Lee C.",
      "year": "1988",
      "journal-title": "Phys. Rev. B"
    },
    {
      "key": "ja028812db00019/ja028812db00019_1",
      "first-page": "728",
      "volume": "54",
      "author": "Ditchfield R.",
      "year": "1971",
      "journal-title": "J. Chem. Phys."
    },
    {
      "key": "ja028812db00019/ja028812db00019_2",
      "first-page": "2261",
      "volume": "56",
      "author": "Hehre W. J.",
      "year": "1972",
      "journal-title": "J. Chem. Phys."
    },
    {
      "key": "ja028812db00019/ja028812db00019_3",
      "doi-asserted-by": "crossref",
      "first-page": "222",
      "DOI": "10.1007/BF00533485",
      "volume": "28",
      "author": "Hariharan P. C.",
      "year": "1973",
      "journal-title": "Theor. Chim. Acta"
    },
    {
      "key": "ja028812db00020/ja028812db00020_1",
      "volume-title": "Gaussian",
      "author": "Frisch M. J.",
      "year": "1998"
    },
    {
      "key": "ja028812db00021/ja028812db00021_1",
      "doi-asserted-by": "crossref",
      "first-page": "417",
      "DOI": "10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W",
      "volume": "19",
      "author": "Barone B.",
      "year": "1998",
      "journal-title": "J. Comput. Chem."
    },
    {
      "key": "ja028812db00022/ja028812db00022_1",
      "volume": "106",
      "author": "After",
      "year": "2002",
      "journal-title": "J. Phys. Chem. A."
    },
    {
      "key": "ja028812db00023/ja028812db00023_1",
      "first-page": "7169",
      "volume": "124",
      "author": "These",
      "year": "2002",
      "journal-title": "J. Am. Chem. Soc."
    }
  ],
  "container-title": "Journal of the American Chemical Society",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://pubs.acs.org/doi/pdf/10.1021/ja028812d",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2021,
        10,
        5
      ]
    ],
    "date-time": "2021-10-05T11:53:45Z",
    "timestamp": 1633434825000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://pubs.acs.org/doi/10.1021/ja028812d"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2003,
        2,
        8
      ]
    ]
  },
  "references-count": 32,
  "journal-issue": {
    "issue": "9",
    "published-print": {
      "date-parts": [
        [
          2003,
          3,
          1
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1021/ja028812d"
  ],
  "URL": "http://dx.doi.org/10.1021/ja028812d",
  "relation": {},
  "ISSN": [
    "0002-7863",
    "1520-5126"
  ],
  "subject": [],
  "container-title-short": "J. Am. Chem. Soc.",
  "published": {
    "date-parts": [
      [
        2003,
        2,
        8
      ]
    ]
  }
}