title: Palladium-catalyzed asymmetric quaternary stereocenter formation.
abstract: An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl(2), PhBOX, and AgSbF(6), and provides products in up to 99% enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands.
authors.forename: Aditya L
authors.initials: AL
authors.lastname: Gottumukkala
authors.forename: Kiran
authors.initials: K
authors.lastname: Matcha
authors.forename: Martin
authors.initials: M
authors.lastname: Lutz
authors.forename: Johannes G
authors.initials: JG
authors.lastname: de Vries
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
mesh_terms: D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D012717:Sesquiterpenes; C518145:alpha-cuparenone; D010165:Palladium