Synthesis and Reactivity of Enantiomerically Pure N-Acyl N-Alkyl p-Toluenesulfinamides

Article abstract of DOI:10.1016/0957-4166(95)00139-G

The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported.Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retension 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.