Ir-Catalyzed Enantioselective Intra- and Intermolecular Formal C−H Conjugate Addition to β-Substituted α,β-Unsaturated Esters

Abstract

An enantioselective intramolecular formal C−H conjugate addition of 4-methyl 1-aryl 2-methylfumarates proceeded using a chiral iridium catalyst. A benzoylamide group served as a directing group, and chiral γ-lactones with a quaternary all-carbon stereogenic center were obtained with up to excellent ee. In the intermolecular reaction of N-arylbenzamides with β-substituted acrylates, C−H bond activation selectively occurred at the ortho-position of carbonyl groups, and highly enantioselective formal C−H conjugate addition proceeded.