Photoenzymatic Hydrosulfonylation for the Stereoselective Synthesis of Chiral Sulfones

Author:

Chen Xiaoyang12,Zheng Dannan1,Jiang Linye1,Wang Zhiguo3,Duan Xinyu1,Cui Dong1,Liu Shuang1,Zhang Yuan2,Yu Xiaomin2,Ge Jingyan1,Xu Jian1ORCID

Affiliation:

1. College of Biotechnology and Bioengineering Zhejiang University of Technology Hangzhou 310014 P. R. China

2. College of Biological, Chemical Science and Engineering Jiaxing University Jiaxing 314001 P. R. China

3. Institute of Aging Research, School of Basic Medical Sciences Hangzhou Normal University Hangzhou 311121 P. R. China

Abstract

AbstractChiral 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).

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Natural Science Foundation of Zhejiang Province

Publisher

Wiley

Subject

General Chemistry,Catalysis

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