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Volumn 71, Issue 7, 2006, Pages 2630-2640

Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to γ-alkoxy-α,β-enoates

Author keywords

[No Author keywords available]

Indexed keywords

ARYLCUPRATE CONJUGATE; KINETIC ISOTOPE EFFECT; TRANSITION STATE;

EID: 33645523429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052383v     Document Type: Article
Times cited : (28)

References (96)
  • 26
    • 0019467942 scopus 로고
    • Reactions of allylcopper reagents seem to be an exception to the "anti-addition" rule, see: Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1981, 103, 1224-1226.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1224-1226
    • Nicolaou, K.C.1    Pavia, M.R.2    Seitz, S.P.3
  • 27
    • 0000110756 scopus 로고
    • For demonstration of the importance of σ*-orbital energies in determining the "large" group in the Felkin model, see: Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3353-3361
    • Lodge, E.P.1    Heathcock, C.H.2
  • 28
    • 0001592452 scopus 로고
    • For selected discussions of the modified Felkin-Ann model, see: (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231-2234.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2231-2234
    • Roush, W.R.1    Lesur, B.M.2
  • 46
  • 50
    • 33645499388 scopus 로고    scopus 로고
    • note
    • A portion of this investigation has been reported, see ref 3r. The remaining results will be detailed in future publications describing the synthetic pathways to the target natural products.
  • 74
    • 33645526192 scopus 로고    scopus 로고
    • Reference 11
    • (d) Reference 11.
  • 78
    • 6244279150 scopus 로고
    • The first evidence for this pathway and its role in the stereochemistry of organocopper addition reactions was disclosed by Corey and Boaz: Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 26, 6015-6018.
    • (1984) Tetrahedron Lett. , vol.26 , pp. 6015-6018
    • Corey, E.J.1    Boaz, N.W.2
  • 84
    • 33645505999 scopus 로고    scopus 로고
    • Reference 6f
    • (c) Reference 6f.
  • 96
    • 33645498982 scopus 로고    scopus 로고
    • note
    • Characterization data of all epimeric mixtures obtained in this work can be found in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.