Work

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

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04701

Authors: Shivani Patel, James D. Finnigan, Jesmine Lim, Nathaniel S. Greenwood, Jonathan A. Ellman

Institutions: Yale University, Prozomix (United Kingdom)

Language: English

Topic: Enzyme Catalysis and Immobilization

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500