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Volumn 126, Issue 30, 2004, Pages 9188-9189

Catalytic enantioselective conjugate addition of carbamates

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYENONE; BENZYL CARBAMATE; BETA AMINO ACID; CARBAMIC ACID DERIVATIVE; COPPER COMPLEX; LEWIS ACID; MAGNESIUM DERIVATIVE; METAL COMPLEX; OXAZOLINE DERIVATIVE; TERT BUTYL CARBAMATE; UNCLASSIFIED DRUG; ZINC COMPLEX;

EID: 3342948302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047004e     Document Type: Article
Times cited : (119)

References (51)
  • 19
    • 0034612973 scopus 로고    scopus 로고
    • Recent review on conjugate additions: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061.
    • (2000) Tetrahedron , vol.56 , pp. 8033-8061
    • Sibi, M.P.1    Manyem, S.2
  • 48
    • 3342889220 scopus 로고    scopus 로고
    • note
    • In acetonitrile, which is the solvent of choice for Cu(II)-catalyzed conjugate additions of carbamates (see ref 13b), the asymmetric reaction did not proceed. THF was also found to be ineffective (<5% conversion after 2 days). Diethyl ether generally showed results comparable to those attained in methylene chloride, although in certain instances the enantioselectivity was essentially perfect (for example, product 11a 92% yield, ≥99% ee; 11b, 95% yield, ≥99% ee).
  • 49
    • 3342882253 scopus 로고    scopus 로고
    • note
    • For problems inherent to the conjugate addition of N-nucleophiles to β-aryl enoyl systems, and a solution to them, see: ref 11c. Also see: ref 11e-g.
  • 50
    • 3342953346 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 51
    • 3342974180 scopus 로고    scopus 로고
    • note
    • At the present stage, proposals for consistent catalytic cycle and transitionstate models seem premature. One reviewer has suggested an eight-membered transition state involving copper coordination.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.