Enantiocontrol and Regiocontrol in Lactam Syntheses by Intramolecular Carbon-Hydrogen Insertion Reactions of Diazoacetamides Catalyzed by Chiral Rhodium(II) Carboxamides.

Abstract Dirhodium(II) catalysts possessing chiral pyrrolidone or oxazolidinone ligands provide moderate enantiocontrol (up to 80% ee) in carbon-hydrogen insertion reactions of N -alkyl- N -( tert -butyl)diazoacetamides; substituents at the 2-position of the N -alkyl group control regioselectivity for β- and γ-lactam formation.