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
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
收藏
页码:2257 / 2260
页数:4
相关论文
共 15 条
[11]   A PETERSON OLEFINATION REACTION USING SILYL-SUBSTITUTED SULFONAMIDE CARBANIONS - SYNTHESIS OF VINYLIC SULFONAMIDES [J].
MLADENOVA, M ;
GAUDEMARBARDONE, F .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 62 (1-4) :257-267
[12]   VINYL SULFONYL ESTERS AND AMIDES IN THE SYNTHESIS OF SUBSTITUTED DELTA-SULTAMS AND DELTA-SULTONES [J].
MORRIS, J ;
WISHKA, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3549-3556
[13]   PROPERTIES AND REACTIONS OF SUBSTITUTED 1,2-THIAZETIDINE 1,1-DIOXIDES - METHYLATION OF BETA-SULTAMS [J].
MULLER, M ;
OTTO, HH .
ARCHIV DER PHARMAZIE, 1991, 324 (01) :15-17
[14]  
MULLER M, 1989, LIEBIGS ANN CHEM, P975
[15]  
OLIVER JE, 1975, SYNTHESIS-STUTTGART, P321