Molybdenum-catalyzed asymmetric sulfoxidation with hydrogen peroxide and subsequent kinetic resolution, using an imidazolium-based dicarboxylate compound as chiral inductor

Abstract

A catalytic system based on simple and economic molybdenum compounds and a straightforwardly prepared imidazolium-based dicarboxylate compound, as chirality inductor, was developed for the catalytic asymmetric oxidation of sulfides with hydrogen peroxide. High yields of chiral methyl phenyl sulfoxide and good enantioselectivities (up to 40% ee) were achieved utilizing one equivalent of oxidant in 1h. By combination of the enantioselective sulfoxidation and the concomitant kinetic resolution an 83% ee was obtained, an excellent enantioselectivity value for a molybdenum catalyst.