Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins

A method for the enantio­selective, intra­molecular sulfeno­amination of various olefins has been developed using a chiral BINAM-based seleno­phosphor­amide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantio­meric ratios via enantio­selective formation and subsequent stereo­specific capture of the thi­iranium intermediate with the pendant tosyl-protected amine.