Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles

Abstract

The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.

Keywords: Lewis acid catalysis; Nazarov reaction; electrocyclization; indole alkaloids.