title: Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.
abstract: A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.
authors.affiliation: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University , Silverman Hall, Evanston, Illinois 60208, United States.
authors.forename: Ki Po
authors.initials: KP
authors.lastname: Jang
authors.forename: Gerri E
authors.initials: GE
authors.lastname: Hutson
authors.forename: Ryne C
authors.initials: RC
authors.lastname: Johnston
authors.forename: Elizabeth O
authors.initials: EO
authors.lastname: McCusker
authors.forename: Paul H-Y
authors.initials: PH
authors.lastname: Cheong
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000215:Acylation; D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003198:Computer Simulation; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006900:Hydroxylation; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D063065:Organophosphonates / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000475:Alkenes; D006571:Heterocyclic Compounds; D063065:Organophosphonates; C030011:carbene; D008697:Methane