Mn-salen catalyzed nitrene transfer reaction: Enantioselective imidation of alkyl aryl sulfides

Abstract

Enantioselective imidation of alkyl aryl sulfides was achieved by using ( R, R)- or ( R, S)-Mn-salen complex [( R, R)-3 or ( R, S)-3] as a catalyst. The optimum reaction conditions are dependent upon the substrates examined. For example, the imidation of alkyl phenyl sulfides with PhI=NTs using Mn-salen complex ( R, R)-3 as a catalyst in the presence of N-methylmorpholine N-oxide showed high enantioselectivity (up to 89% ee). On the other hand, the reaction of methyl 2,4-dinitrophenyl sulfide was effected (97% ee) by using Mn-salen complex ( R, S)-3 as the catalyst in the absence of N-methylmorpholine N-oxide.