A highly stereo-divergent Mannich-type reaction catalyzed by Bronsted acid in aqueous media

被引：53
作者：
Akiyama, T [1 ]
Takaya, J [1 ]
Kagoshima, H [1 ]
机构：
[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 24期
关键词：
Bronsted acid; diastereoselectivity; Mannich-type reactions; Schiff bases; water;
D O I：
10.1016/S0040-4039(01)00648-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
anti And syn stereoselectivity on the HBF4-catalyzed Mannich-type reaction of ketene silyl acetal derived from cc-oxy esters with aldimines were investigated. Whereas use of ketene silyl acetal derived from aryl ester in aqueous 2-propanol gave anti beta -amino-alpha -siloxy ester with excellent stereoselectivity, use of ketene silyl acetal derived from methyl ester in water in the presence of sodium dodecyl sulfate gave the syn isomer preferentially. (C) 2001 Elsevier Science Ltd. All rights reserved.
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收藏
页码：4025 / 4028
页数：4
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