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Stereospecific CN Bond Cleavage of 4-Silylated 1, 2-Thiazetidine 1, 1-Dioxides with EtAlCl2 or AlCl3: Formation of (E)-Vinylsulfonamides.

T Iwama, A Takagi, T Kataoka

Index: Iwama, Tetsuo; Takagi, Atsuko; Kataoka, Tadashi Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 5 p. 757 - 766

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Citation Number: 16

Abstract

Monosilylation of 1, 2-thiazetidine 1, 1-dioxides (β-sultams) 3 gave (3R*, 4S*)-4-monosilyl-β- sultams 4 stereoselectively. Disilylated β-sultams 5 were obtained by the use of trimethylsilyl chloride. Treatment of 4-monosilyl-β-sultams 4 with EtAlCl 2 caused stereospecific CN bond cleavage owing to β-cation stabilization of the silicon group to provide (E)-vinylsulfonamides (E)-7.(E)-α-Silylstyrylsulfonamides (E)-7j-l were generated in the reaction of 4, 4-disilyl-β- ...

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