Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides

A peptide-catalyzed enantioselective oxidation of sulfides
to yield
pharmaceutically relevant chiral sulfoxides is reported. Experimental
evidence suggesting that a hydrogen bond-donating moiety must be present
in the substrate to achieve high levels of enantioinduction is supported
by computational modeling of transition states. These models also
indicate that dual points of contact between the peptidic catalyst
and substrate are likely responsible for the formation of one desired
sulfoxide in 94:6 er.