Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C–H Bond to Aldehydes To Afford Enantioenriched Phthalides
Wenkun Chen, Jie Li, Hui Xie, Jun Wang
Abstract
An asymmetric rhodium(III)-catalyzed Grignard-type addition of inert arene C–H bond to aldehydes is reported. It provides a new strategy for the synthesis of chiral 3-substituted phthalides in good yields (up to 87%) with high enantiomeric purity (up to 99% ee). Interestingly, a chiral-matching effect between substrate and catalyst was observed, which is crucial to accomplish satisfied reaction outcomes. Mechanistically, the reaction is assumed to proceed via consecutive C(sp2)–H activation of benzamide, addition to aldehyde, and lactonization.
Topics & Concepts
ChemistryBenzamideRhodiumCatalysisAldehydeEnantioselective synthesisEnantiomerSubstrate (aquarium)InertMedicinal chemistryCombinatorial chemistryOrganic chemistryStereochemistryOceanographyGeologyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms