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

• DOI: 10.1021/acs.orglett.4c02452
• Publication Date: 2024-08-05T16:57:00Z
• Authors: Susannah E. Huth; Nicolò Tampellini; Maria D. Guerrero; Scott J. Miller
• Keywords: Sulfoxide; Moiety; Transition state

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 achieve high levels enantioinduction supported by computational modeling transition states. These models also indicate dual points contact between peptidic catalyst and are likely responsible for formation one desired sulfoxide 94:6 er.