Affiliation:
1. International Joint Research Center for Molecular Science College of Chemistry and Environmental Engineering College of Physics and Optoelectronic Engineering Shenzhen University Shenzhen 518060 P. R. China
2. School of Chemistry and Chemical Engineering Pingyuan Laboratory Henan Normal University Xinxiang Henan 453007 P. R. China
3. Key Laboratory of Natural Medicine and Immuno‐Engineering of Henan Province Henan University Kaifeng Henan 475004 P. R. China
Abstract
AbstractAn unprecedented enantioselective protonation reaction enabled by photoredox catalytic radical coupling is developed. Under cooperative dicynopyrazine‐derived chromophore (DPZ) as a photosensitizer and a chiral phosphoric acid catalyst, and Hantzsch ester as a sacrificial reductant, the transformations between α‐substituted enones and cyanoazaarenes or 2‐(chloromethyl)azaaren‐1‐iums can proceed a tandem reduction, radical coupling, and enantioselective protonation process efficiently. Two classes of pharmaceutically important enantioenriched azaarene variants, which contain a synthetically versatile ketone‐substituted tertiary carbon stereocenter at the β‐ or γ‐position of the azaarenes, are synthesized with high yields and ees.
Funder
National Natural Science Foundation of China
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
Subject
General Physics and Astronomy,General Engineering,Biochemistry, Genetics and Molecular Biology (miscellaneous),General Materials Science,General Chemical Engineering,Medicine (miscellaneous)