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Volumn 46, Issue 41, 2010, Pages 7799-7800

Enantioselective conjugate addition of boronic acids to enones catalyzed by O-monoacyltartaric acids

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DI(TERT BUTYL)BENZOYL; BORONIC ACID DERIVATIVE; ENONE DERIVATIVE; KETONE DERIVATIVE; O MONOACYLTARTARIC ACID; PEROXIDE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77957839988     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc03076g     Document Type: Article
Times cited : (58)

References (27)
  • 2
    • 33745210040 scopus 로고    scopus 로고
    • D. G. Hall, Wiley-VCH, Weinheim, For 1,4-addition to enones catalyzed by chiral biphenols, see:
    • R. A. Batey, in Boronic Acids, ed., D. G. Hall,, Wiley-VCH, Weinheim, 2005, ch. 7
    • (2005) Boronic Acids, Ed.
    • Batey In, R.A.1
  • 15
    • 50549097452 scopus 로고    scopus 로고
    • Yamamoto et al. employed boron complexes of O-monoacyltartaric acids as asymmetric Lewis acid catalysts for Diels-Alder reactions, aldol-type reactions, allylations, etc., and found 2,6-dialkoxybenzoyl derivatives to be effective. For leading references, see:
    • S.-G. Kim Tetrahedron Lett. 2008 49 6148
    • (2008) Tetrahedron Lett. , vol.49 , pp. 6148
    • Kim, S.-G.1
  • 26
    • 33745210040 scopus 로고    scopus 로고
    • D. G. Hall, Wiley-VCH, Weinheim, The addition of methanol (1 equiv.) or the use of water or tert-butylalcohol (2 equiv.) instead of methanol afforded comparable results. However, methanol (4 equiv.) cut in the yield in half. It has recently been reported that the presence of a small amount of alcohol improves the outcome of binaphthol-catalyzed allylboration of ketones, see ref. 3b O-Monoacylated l-tartaric acids were prepared via monoacylation of dibenzyl l-tartarate and subsequent hydrogenolysis of the benzyl esters, according to the reported procedure, see:
    • D. G. Hall, Boronic Acids, ed., D. G. Hall,, Wiley-VCH, Weinheim, 2005, ch. 1
    • (2005) Boronic Acids, Ed.
    • Hall, D.G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.