Visible-Light-Driven Enantioselective Radical Addition to Imines Enabled by the Excitation of a Chiral Phosphoric Acid–Imine Complex
Tatsuhiro Uchikura, Nanami Kamiyama, Toshiki Mouri, Takahiko Akiyama
Abstract
A visible-light-driven enantioselective radical addition to imines enabled by the direct excitation of a chiral phosphoric acid–imine complex was developed. By using benzothiazolines as the radical precursors, chiral amine products were obtained with high enantioselectivities (up to 98% ee). Mechanistic studies elucidated that the chiral phosphoric acid–imine complex has photoredox activities for oxidizing benzothiazolines.
Topics & Concepts
ImineEnantioselective synthesisPhosphoric acidChemistryOxidizing agentPhotochemistryAmine gas treatingCombinatorial chemistryCatalysisPhotoredox catalysisOrganic chemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques