title: Asymmetric autocatalysis: triggered by chiral isotopomer arising from oxygen isotope substitution.
abstract: Trigger happy: chiral oxygen isotopomers of hydrobenzoin ([(18)O](R)-1 and [(18)O](S)-1) acted as chiral triggers to induce the enantioselective addition of iPr(2)Zn to pyrimidine-5-carbaldehyde. An extremely small chiral influence arising from the presence of the oxygen isotope ((18)O) is amplified through asymmetric autocatalysis to enantioenrich the 5-pyrimidyl alkanol product.
authors.affiliation: Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Japan. tkawa@rs.kagu.tus.ac.jp
authors.forename: Tsuneomi
authors.initials: T
authors.lastname: Kawasaki
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Okano
authors.forename: Etsuharu
authors.initials: E
authors.lastname: Suzuki
authors.forename: Shizuka
authors.initials: S
authors.lastname: Takano
authors.forename: Shotaro
authors.initials: S
authors.lastname: Oji
authors.forename: Kenso
authors.initials: K
authors.lastname: Soai
mesh_terms: D001573:Benzoin / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D010103:Oxygen Isotopes / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D010103:Oxygen Isotopes; D011743:Pyrimidines; C540375:hydrobenzoin; D015032:Zinc; C030986:pyrimidine; D001573:Benzoin