title: Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst.
abstract: The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral beta-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.
authors.affiliation: P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Jeung Gon
authors.initials: JG
authors.lastname: Kim
authors.forename: Elizabeth H
authors.initials: EH
authors.lastname: Camp
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
chemical_list: D007659:Ketones; D014025:Titanium