title: 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.
authors.affiliation: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China).
authors.forename: Zijun
authors.initials: Z
authors.lastname: Wu
authors.forename: Fangyi
authors.initials: F
authors.lastname: Li
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D007783:Lactones; D058116:Lewis Acids; D008698:Mesylates; C030011:carbene; C012077:trifluoromethanesulfonic acid; D008697:Methane
keywords: N-heterocyclic carbene; annulation; dynamic kinetic resolution; lactones; oxidative addition