title: Enantioselective synthesis of alpha-substituted ketones by asymmetric addition of chiral zinc enamides to 1-alkenes.
abstract: A zinc enamide of a chiral imine derived from a ketone and (S)-valinol or (S)-t-leucinol undergoes addition to 1-alkene to generate a gamma-zincioimine intermediate, which reacts with a carbon electrophile to give upon hydrolysis an optically active alpha-substituted ketone in good yield. The stereoselectivity of the addition reaction may reach 99% for the reaction of a cyclohexanone imine with ethylene.
authors.affiliation: Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Masaharu
authors.initials: M
authors.lastname: Nakamura
authors.forename: Takuji
authors.initials: T
authors.lastname: Hatakeyama
authors.forename: Kenji
authors.initials: K
authors.lastname: Hara
authors.forename: Eiichi
authors.initials: E
authors.lastname: Nakamura