SYNTHESIS AND REACTIVITY OF ENANTIOMERICALLY PURE N-ACYL N-ALKYL P-TOLUENESULFINAMIDES

The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesu lfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p- tolylsulfinate followed by N-acylation of the resulting sulfinamides a re reported. Their reactions with some C-nucleophiles take place at th e sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense , their comparison with other reagents popularly used, revealed that 5 have some important advantages.