Intermolecular dynamic kinetic resolution cooperatively catalyzed by an N-heterocyclic carbene and a Lewis acid

Abstract

The ubiquitous structure of δ-lactones makes the development of new methods for their enantioselective and stereoselective synthesis an important ongoing challenge. The intermolecular dynamic kinetic resolution (DKR) of β-halo-α-ketoesters cooperatively catalyzed by an N-heterocyclic carbene and a Lewis acid generates two contiguous stereocenters with remarkable diastereoselectivity through an oxidation/lactonization sequence.