Biocatalytic Enantioselective Oxidation of N -Acyl- S -Methyl Sulfenamides for the Asymmetric Synthesis of S -Methyl Sulfoximines

Enantioenriched sulfinamides serve as key intermediates for the asymmetric synthesis of sulfoximines and other S(VI) pharmacophores. Enantioselective biocatalytic oxidation of an S-methyl sulfenamide to the corresponding S-methyl sulfinamide proceeds in good yield and >99:1 er. Its utility as a key chiral intermediate was demonstrated by stereoretentive S-arylation and S-alkylation as well as by the asymmetric synthesis of two S-methyl sulfoximine drug candidates, with S-methyl substitution notably present in most sulfoximine clinical candidates.