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Volumn 63, Issue 24, 1998, Pages 8998-9006

Origin of enantioselectivities in chiral β-amino alcohol catalyzed asymmetric additions of organozinc reagents to benzaldehyde: PM3 transition state modeling

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMINOALCOHOL; BENZALDEHYDE; BETA AMINO ACID; CAMPHOR; ETHANE; PROLINE DERIVATIVE;

EID: 0031791876     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9813787     Document Type: Article
Times cited : (117)

References (38)
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  • 5
    • 0001956304 scopus 로고
    • For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (b) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p 255. (d) Evans, D. A. Science 1988, 240, 420.
    • (1991) Angew. Chem. , vol.103 , pp. 34
    • Noyori, R.1    Kitamura, M.2
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    • For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (b) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p 255. (d) Evans, D. A. Science 1988, 240, 420.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 49
  • 7
    • 0003400107 scopus 로고
    • Wiley: New York
    • For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (b) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p 255. (d) Evans, D. A. Science 1988, 240, 420.
    • (1994) Asymmetric Catalysis in Organic Synthesis , pp. 255
    • Noyori, R.1
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    • 0024294399 scopus 로고
    • For reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (b) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p 255. (d) Evans, D. A. Science 1988, 240, 420.
    • (1988) Science , vol.240 , pp. 420
    • Evans, D.A.1
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    • Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. The activation energy of the reaction (∼14 kcal/mol) and the energy difference between (R)-and (S)-TS (3.6 kcal/mol) were computed, but no detailed descriptions of the transition structures were given.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1391
    • Nakano, H.1    Kumagai, N.2    Matsuzaki, H.3    Kabuto, C.4    Hongo, H.5
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    • note
    • in groups and the zinc chelate ring and for the anti structures from close distances between the Phin groups and the alkyl groups (R) attached to zinc: equation presented
  • 35
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    • For PM3 parameters, see: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221; J. Comput. Chem. 1991, 12, 320.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209
    • Stewart, J.J.P.1
  • 36
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    • For PM3 parameters, see: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221; J. Comput. Chem. 1991, 12, 320.
    • (1991) J. Comput. Chem. , vol.12 , pp. 320
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.