Catalytic, Enantioselective Aziridine Desymmetrization with Pyrroles

Abstract

Ring-opening reactions of meso-aziridines with carbon nucleophiles lead to complex, enantioenriched chiral amine derivatives through enantioselective catalysis. We report that a diphosphine-palladium(II) catalyst enables the highly enantioselective desymmetrization of N-acylaziridines with pyrroles. The β-pyrrole amine products are isolated with excellent enantioselectivity and varying yields across a range of pyrrole and aziridine substitution patterns. The synthetic utility of the pyrrole products is demonstrated by conversion to a novel saturated pyrrolopyridine core.