Enantioselective Synthesis of Diaryl Sulfoxides Enabled by Molecular Recognition

The enantioselective sulfoxidation of diaryl-type sulfides was accomplished using a chiral manganese porphyrin complex equipped with a remote molecular recognition site. Despite the marginal size difference between the two substituents at the prostereogenic sulfur center, hydrogen bonding enabled the formation of chiral sulfoxides with exquisite enantioselectivities (16 examples, up to 99% ee). Aside from the precise orientation of a distinct substrate, the quinolone lactam offers an excellent entry point for further derivatization.