title: Scandium-catalyzed allylboration of aldehydes as a practical method for highly diastereo- and enantioselective construction of homoallylic alcohols.
abstract: A general approach for the allylation of aldehydes using stable, air-tolerant camphor-based chiral allylboronates under Sc(OTf)3 catalysis is described. This practical methodology provides both syn and anti propionate units and other homoallylic alcohols with very high levels of diastereo- and enantioselectivity for several substrates, including functionalized aliphatic aldehydes useful toward the elaboration of complex natural products.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Hugo
authors.initials: H
authors.lastname: Lachance
authors.forename: Xiaosong
authors.initials: X
authors.lastname: Lu
authors.forename: Michel
authors.initials: M
authors.lastname: Gravel
authors.forename: Dennis G
authors.initials: DG
authors.lastname: Hall
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D001897:Boronic Acids; D012538:Scandium