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A Photoenzymatic Strategy for Radical-Mediated Stereoselective Hydroalkylation with Diazo Compounds |
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| Authors: | Xinyu Duan Dong Cui Zhiguo Wang Dannan Zheng Linye Jiang Wen-Yu Huang Yi-Xia Jia Jian Xu |
| Institution: | 1. College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P. R. China
These authors contributed equally to this work.;2. Institute of Aging Research, School of Basic Medical Sciences, Hangzhou Normal University, Hangzhou, 311121 P. R. China These authors contributed equally to this work.;3. College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 P. R. China;4. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014 P. R. China |
| Abstract: | Carbene insertion reactions initiated with diazo compounds have been widely used to develop unnatural enzymatic reactions. However, alternative functionalization of diazo compounds in enzymatic processes has been unexploited. Herein, we describe a photoenzymatic strategy for radical-mediated stereoselective hydroalkylation with diazo compounds. This method generates carbon-centered radicals through an ene reductase catalyzed photoinduced electron transfer process from diazo compounds, enabling the synthesis of γ-stereogenic carbonyl compounds in good yields and stereoselectivities. This study further expands the possible reaction patterns in photo-biocatalysis and offers a new approach to solving the selectivity challenges of radical-mediated reactions. |
| Keywords: | Diazo Compounds Hydroalkylation Photo-Biocatalysis Radicals |