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Volumn 63, Issue 30, 2007, Pages 7036-7046

Asymmetric synthesis of β-substituted Baylis-Hillman products via lithium amide conjugate addition

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; LITHIUM;

EID: 34249988237     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.05.015     Document Type: Article
Times cited : (13)

References (58)
  • 1
    • 34250000732 scopus 로고    scopus 로고
    • Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972.
  • 3
    • 34249999919 scopus 로고    scopus 로고
    • For selected reviews, see:
  • 37
    • 34249989591 scopus 로고    scopus 로고
    • For selected uses of lithium N-methyl-N-(α-methylbenzyl)amide 9 in asymmetric synthesis, see:
  • 46
    • 34250015983 scopus 로고    scopus 로고
    • note
    • 1H NMR chiral shift experiments with (R)-O-acetyl mandelic acid and comparison with an authentic scalemic sample.
  • 47
    • 34250000468 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopic analysis of the crude reaction product.
  • 51
    • 34250008936 scopus 로고    scopus 로고
    • note
    • -1; retention times: (S)-enantiomer 9 min, (R)-enantiomer 16 min.
  • 52
    • 34249995618 scopus 로고    scopus 로고
    • note
    • A known scalemic mixture of lithium N-methyl-N-(α-methylbenzyl)amide 9 (33% ee, enriched in (R)-9) was used in the same three-step protocol (conjugate addition, aldol and Cope elimination) to generate authentic material of 33% ee to allow unambiguous ee determination.
  • 53
    • 34250006431 scopus 로고    scopus 로고
    • note
    • The major diastereoisomer in each case was assigned the syn-configuration by analogy to that unambiguously confirmed upon aldol reaction of 10 and 11 with acetaldehyde.
  • 54
    • 34249993691 scopus 로고    scopus 로고
    • note
    • -1; retention times: (S)-enantiomer 11 min, (R)-enantiomer 18 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.