Enantioselective Radical Hydrocyanoalkylation of Alkenes via Photoenzymatic Catalysis.

ABSTRACT: Organic nitriles are significant in pharmaceuticals, agrochemicals, cosmetics, and materials. Although numerous cyanidation methods have been developed, more eco-friendly and green protocols for manufacturing alkyl nitriles are in high demand. Here, we report a photoenzymatic enantioselective intermolecular hydrocyanoalkylation of alkenes catalyzed by flavin-dependent "ene"-reductases. The discovery of stereocomplementary enzymes that provide access to both enantiomers of the high-value nitriles further showcases the synthetic applications of this method. Radical trapping, isotopic labeling, and spectroscopic experiments have elucidated the formation of a charge transfer complex at the protein active site. The single-electron reduction of the cyanoalkyl radical precursor by flavin hydroqui

SUBMITTER: Wu D 

PROVIDER: S-EPMC12308436 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature