New Chemical Aspects of ß -Sultams: Selective Hetero Bond Cleavage and Sequential Reactions

Abstract

The selective C-S bond cleavage of a β-sultam ring was achieved using EtAlCl2 as a Lewis acid. Furthermore, treatment of 4-silyl-β -sultams with EtAlCl2 effected the selective C-N bond cleavage which, followed by desilylation, afforded (E)-vinylsulfonamides stereospecifically. The Pummerer reaction of 4-sulfenyl- β -sultams produced α-amino acid thioesters, and the chiral α-amino acid thioesters were prepared from chiral imines and methanesulfonyl chloride.