title: NHC-catalyzed/titanium(IV)-mediated highly diastereo- and enantioselective dimerization of enals.
abstract: An NHC-catalyzed, diastereo- and enantioselective dimerization of enals has been developed. The use of Ti(Oi-Pr)(4) is a key element for the reactivity and selectivity of this process. The cyclopentenes are obtained with high levels of diastereo- and enantioselectivity and their synthetic utility is demonstrated by functionalization of the product alkene.
authors.affiliation: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, Illinois 60208, USA.
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Cohen
authors.forename: Benoit
authors.initials: B
authors.lastname: Cardinal-David
authors.forename: John M
authors.initials: JM
authors.lastname: Roberts
authors.forename: Amy A
authors.initials: AA
authors.lastname: Sarjeant
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D058116:Lewis Acids / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D003517:Cyclopentanes; D058116:Lewis Acids; C030011:carbene; D014025:Titanium; D008697:Methane