Selective C-N bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl2: Stereospecific formation of (E)-vinylsulfonamides

Article abstract of DOI:10.1016/0040-4039(96)00269-9

Monosilylation of 1,2-thiazetidine 1,1-dioxides (β-sultams) furnished (3R*, 4S*)-4-silylated β-sultams stereoselectively. Treatment of 4-silylated β-sultams with a Lewis acid caused the selective C-N bod cleavage because of the β-silyl stabilization against the resultant carbenium ion followed by desilation to provide (E)-vinylsulfonamides stereospecifically.