title: A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.
abstract: A dual activation strategy integrating N-heterocyclic carbene (NHC) catalysis and a second Lewis base has been developed. NHC-bound homoenolate equivalents derived from α,β-unsaturated aldehydes combine with transient reactive o-quinone methides in an enantioselective formal [4 + 3] fashion to access 2-benzoxopinones. The overall approach provides a general blueprint for the integration of carbene catalysis with additional Lewis base activation modes.
authors.affiliation: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, USA.
authors.forename: Javier
authors.initials: J
authors.lastname: Izquierdo
authors.forename: Ane
authors.initials: A
authors.lastname: Orue
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry; D002384:Catalysis; D045563:Indolequinones / Q000737:chemistry; D058115:Lewis Bases / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001555:Benzene Derivatives; D045563:Indolequinones; D058115:Lewis Bases; C068040:quinone methide; C030011:carbene; D008697:Methane