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Volumn 62, Issue 15, 1997, Pages 4970-4982

Synthesis of a family of fine-tunable new chiral ligands for catalytic asymmetric synthesis. Ligand optimization through the enantioselective addition of diethylzinc to aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 1,2 DIOL DERIVATIVE; ALCOHOL DERIVATIVE; BENZALDEHYDE; UNCLASSIFIED DRUG;

EID: 0030739748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701445     Document Type: Article
Times cited : (123)

References (70)
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    • For compilations of natural and non-natural enantioselective catalysts and auxiliaries, see, for example: (a) Blaser, H. U. Chem. Rev. 1992, 92, 935-952. (b) Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Seyden-Penne, J., Ed.; John Wiley & Sons, Inc.: New York, 1995.
    • (1992) Chem. Rev. , vol.92 , pp. 935-952
    • Blaser, H.U.1
  • 5
    • 0742318457 scopus 로고
    • John Wiley & Sons, Inc.: New York
    • For compilations of natural and non-natural enantioselective catalysts and auxiliaries, see, for example: (a) Blaser, H. U. Chem. Rev. 1992, 92, 935-952. (b) Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Seyden-Penne, J., Ed.; John Wiley & Sons, Inc.: New York, 1995.
    • (1995) Chiral Auxiliaries and Ligands in Asymmetric Synthesis
    • Seyden-Penne, J.1
  • 16
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    • Reference 1b, pp 101-158
    • (b) Reference 1b, pp 101-158.
  • 17
    • 0001780886 scopus 로고    scopus 로고
    • Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York
    • (c) Katsuki, T.; Martin, V. S. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1996; Vol. 48, pp 1-299.
    • (1996) Organic Reactions , vol.48 , pp. 1-299
    • Katsuki, T.1    Martin, V.S.2
  • 25
    • 8544282215 scopus 로고    scopus 로고
    • note
    • Similar ligands derived from other epoxides are currently studied in our laboratories. The results of these studies will be reported in due time.
  • 33
    • 0003405157 scopus 로고
    • Georg Thieme Verlag: Stuttgart
    • (b) Protecting Groups; Kocienski, P. J., Ed.; Georg Thieme Verlag: Stuttgart 1994; pp 58.
    • (1994) Protecting Groups , pp. 58
    • Kocienski, P.J.1
  • 41
    • 8544220183 scopus 로고    scopus 로고
    • For related examples see ref 4f,g
    • For related examples see ref 4f,g.
  • 42
    • 8544271417 scopus 로고    scopus 로고
    • Reference 1a, Chapter 5, pp 255-297
    • For reviews on the enantioselective addition of organometallic reagents to carbonyl compounds see: (a) Reference 1a, Chapter 5, pp 255-297. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (c) Soai, K. Chem. Rev 1992, 92, 833-856.
  • 43
    • 33748247006 scopus 로고
    • For reviews on the enantioselective addition of organometallic reagents to carbonyl compounds see: (a) Reference 1a, Chapter 5, pp 255-297. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (c) Soai, K. Chem. Rev 1992, 92, 833-856.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 49-69
    • Noyori, R.1    Kitamura, M.2
  • 44
    • 4244117250 scopus 로고
    • For reviews on the enantioselective addition of organometallic reagents to carbonyl compounds see: (a) Reference 1a, Chapter 5, pp 255-297. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (c) Soai, K. Chem. Rev 1992, 92, 833-856.
    • (1992) Chem. Rev , vol.92 , pp. 833-856
    • Soai, K.1
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    • (c) Noyori, R. Science 1990, 248, 1194-1199.
    • (1990) Science , vol.248 , pp. 1194-1199
    • Noyori, R.1
  • 59
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    • and references cited therein
    • See, for example: Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264-4268 and references cited therein.
    • (1991) J. Org. Chem. , vol.56 , pp. 4264-4268
    • Soai, K.1    Yokoyama, S.2    Hayasaka, T.3
  • 61
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    • note
    • The optimal amount of ligand was determined for 4d as follows: Using a 3% molar amount of ligand, and performing the reaction in hexane, conversion was 96% after 21 h and the enantiomeric excess of the resulting alcohol was 84%. With a 6% molar amount of ligand, conversion was >99% after 3 h, and ee was 89%. No further improvement m enantioselectivity was recorded by increasing the amount of ligand employed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.