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.