Enantioselective aldol reaction with a bromofluoroketene silyl acetal catalyzed by a chiral Lewis acid

被引:28
作者
Iseki, K
Kuroki, Y
Kobayashi, Y
机构
[1] MEC Laboratory, Daikin Industries, Ltd., Miyukigaoka, Tsukuba
关键词
D O I
10.1016/S0040-4039(97)01717-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bromofluoroketene silyl acetal 1 was prepared in pure form. Aldol reactions of 1 with achiral aldehydes catalyzed by chiral Lewis acid 2 proceeded with high enantioselectivity to give optically active syn- and anti-alpha-bromo-alpha-fluoro-beta-hydroxy esters 3a-h, respectively (up to 99% ee). (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7209 / 7210
页数:2
相关论文
共 14 条
[1]   PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS [J].
BRAVO, P ;
RESNATI, G .
TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :661-692
[2]  
Filler R., 1982, BIOMEDICAL ASPECTS F
[3]  
IMURA K, 1995, 19 FLUOR C JAP OK
[4]  
IMURA K, 1996, 20 FLUOR C JAP NAG
[5]   Isolation of alpha,alpha-difluoroketene silyl acetal and its application to asymmetric aldol reactions [J].
Iseki, K ;
Kuroki, Y ;
Asada, D ;
Kobayashi, Y .
TETRAHEDRON LETTERS, 1997, 38 (08) :1447-1448
[6]  
ISHIHARA T, 1994, 14 INT S FLUOR CHEM
[7]  
ISHIHARA T, 1997, 72 NAT M CHEM SOC JA
[8]  
MIMA K, 1997, 72 NAT M CHEMS OC JA
[9]  
Ojima I., 1996, BIOMEDICAL FRONTIERS
[10]   THE CATALYTIC ASYMMETRIC ALDOL REACTION OF ALDEHYDES WITH UNSUBSTITUTED AND MONOSUBSTITUTED SILYL KETENE ACETALS - FORMATION OF ANTI-BETA-HYDROXY-ALPHA-METHYL ESTERS [J].
PARMEE, ER ;
HONG, YP ;
TEMPKIN, O ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1992, 33 (13) :1729-1732