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.

引用

页码：2257 / 2260

页数：4

共 50 条

[1] Selective C-N bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl2: stereospecific formation of (E)-vinylsulfonamides
Tetrahedron Lett, 13 (2257):
[2] Stereospecific C-N bond cleavage of 4-silylated 1,2-thiazetidine 1,1-dioxides with EtAlCl2 or AlCl3:: Formation of (E)-vinylsulfonamides
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