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Volumn 45, Issue 33, 2006, Pages 5502-5505

A priori theoretical prediction of selectivity in asymmetric catalysis: Design of chiral catalysts by using quantum molecular interaction fields

Author keywords

Asymmetric addition; Benzaldehyde; Enantioselectivity; Structure activity relationships; Zinc

Indexed keywords

ASYMMETRIC ADDITION; BENZALDEHYDE; ENANTIOSELECTIVITY; STRUCTURE-ACTIVITY RELATIONSHIPS;

EID: 33748668003     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600329     Document Type: Article
Times cited : (87)

References (40)
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    • For comments on the complexity of the transition state calculations: c) T. Rasmussen, P.-O. Norrby, J. Am. Chem. Soc. 2003, 125, 5130-5138.
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    • and references therein
    • b) L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757, and references therein.
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    • Pu, L.1    Yu, H.-B.2
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    • With homochiral catalysts, syn dimers have been observed experimentally: a) E. Hecht, Z. Anorg. Allg. Chem. 2000, 626, 2223-2227;
    • (2000) Z. Anorg. Allg. Chem. , vol.626 , pp. 2223-2227
    • Hecht, E.1
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    • personal communication
    • a) W. A. Nugent, personal communication;
    • Nugent, W.A.1
  • 31
    • 0037756810 scopus 로고    scopus 로고
    • b) Subsequent to our calculations a report of 81 % ee for P3 in this same reaction appeared: S. N. Joshi, S. V. Malhotra, Tetrahedron: Asymmetry 2003, 14, 1763-1766.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1763-1766
    • Joshi, S.N.1    Malhotra, S.V.2
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    • 0030665236 scopus 로고    scopus 로고
    • See the Supporting Information for further details and full characterization. Epoxidation was accomplished with Shi's protocol (Z. Wang, Y. Tu, M. Frohn, J. Zhang, Y. Shi, J. Am. Chem. Soc. 1997, 119, 11 224-11 235) and epoxide opening with Singaram's conditions (see reference [14]).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11224-11235
    • Wang, Z.1    Tu, Y.2    Frohn, M.3    Zhang, J.4    Shi, Y.5
  • 33
    • 33748643514 scopus 로고    scopus 로고
    • note
    • The enantiomers of the predicted catalysts P1, P4, and P5 were synthesized and yielded the enantiomer (R) opposite to that predicted (S).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.