Stereoselective synthesis of epoxides by reaction of donor/acceptor-substituted carbenoids with α,β-unsaturated aldehydes

被引:63
作者
Davies, HML [1 ]
DeMeese, J [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(01)01415-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of donor/acceptor-substituted carbenoids with alpha,beta -unsaturated aldehydes results in the highly diastereoselective synthesis of epoxides. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:6803 / 6805
页数:3
相关论文
共 14 条
[1]   Asymmetric synthesis of 1-alkynylcyclopropane-1-carboxylates [J].
Davies, HML ;
Boebel, TA .
TETRAHEDRON LETTERS, 2000, 41 (43) :8189-8192
[2]   Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].
Davies, HML ;
Bruzinski, PR ;
Lake, DH ;
Kong, N ;
Fall, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907
[3]   Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity [J].
Davies, HML ;
Panaro, SA .
TETRAHEDRON, 2000, 56 (28) :4871-4880
[4]   Recent progress in asymmetric intermolecular C-H activation by rhodium carbenoid intermediates [J].
Davies, HML ;
Antoulinakis, EG .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :47-55
[5]  
Davies HML, 1999, EUR J ORG CHEM, V1999, P2459
[6]   Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].
Davies, HML ;
Bruzinski, PR ;
Fall, MJ .
TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136
[7]  
DAVIES HML, 2001, IN PRESS J ORG CHEM
[8]  
Doyle M.P., 1998, MODERN CATALYTIC MET, P112
[9]   Epoxides and aziridines from diazoacetates via ylide intermediates [J].
Doyle, MP ;
Hu, WH ;
Timmons, DJ .
ORGANIC LETTERS, 2001, 3 (06) :933-935
[10]   Stereocontrol in intermolecular dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans [J].
Doyle, MP ;
Forbes, DC ;
Protopopova, MN ;
Stanley, SA ;
Vasbinder, MM ;
Xavier, KR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7210-7215