Photoenzymatic Hydrosulfonylation for the Stereoselective Synthesis of Chiral Sulfones

A photoenzymatic strategy for radical-mediated stereoselective hydrosulfonylation has been developed. An engineered OYE1 enzyme enabled the generation of a series of β-chiral sulfonyl compounds in high yields (up to 92 %) with excellent e.r. values (up to 99 : 1).

Abstract

Chiral sulfones are recurrent motifs in pharmaceuticals and bioactive molecules. Although chemical methods have been developed to afford α- or β- chiral sulfones, these protocols rely heavily on the pre-synthesis of structurally complicated starting materials and chiral metal complexes. Herein, we described a photoenzymatic approach for the radical-mediated stereoselective hydrosulfonylation. Engineered variants of ene reductases provide efficient biocatalysts for this transformation, enabling to achieve a series of β-chiral sulfonyl compounds with high yields (up to 92 %) and excellent e.r. values (up to 99 : 1).

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