Asymmetric Sulfur Oxidation Mediated by Camphorsulfonylimines

Abstract

Catalytic enantioselective oxidation of a range of sulfides is achieved in very high yields by treatment with hydrogen peroxide in conjunction with enantiomerically pure sulfonylimines under basic conditions. Enantioselectivities of up to ca. 98% or better were obtained using acetals of oxocamphorsulfonylimine as mediators. This process is clean, inexpensive and simple, requires minimum work up and no close monitoring. The reactive intermediate is currently formulated as an α-hydroperoxyamine.

Keywords::

• Organosulfur
• sulfide
• sulfoxide
• asymmetric oxidation