Selective C-N bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl(2): Stereospecific formation of (E)-vinylsulfonamides

被引：10
|
作者：
Kataoka, T
Iwama, T
Takagi, A
机构：
[1] Gifu Pharmaceutical University, Gifu 502, 6-1
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期
关键词：
D O I：
10.1016/0040-4039(96)00269-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Monosilylation of 1,2-thiazetidine 1,1-dioxides (beta-sultams) furnished (3R*, 4S*)-4-silylated beta-sultams stereoselectively. Treatment of 4-silylated beta-sultams with a Lewis acid caused the selective C-N bond cleavage because of the beta-silyl stabilization against the resultant carbenium ion followed by desilylation to provide (E)-vinylsulfonamides stereospecifically.
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页码：2257 / 2260
页数：4
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