title: Asymmetric α-hydroxylation of tetralone-derived β-ketoesters by using a guanidine-urea bifunctional organocatalyst in the presence of cumene hydroperoxide.
abstract: Highly enantioselective catalytic oxidation of 1-tetralone-derived β-keto esters was achieved by using a guanidine-urea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP), a safe, commercially available oxidant. The α-hydroxylation products were obtained in 99% yield with up to 95% enantiomeric excess (ee). The present oxidation was successfully applied to synthesize a key intermediate of the anti-cancer agent daunorubicin (2).
authors.affiliation: Department of Biotechnology and Life Science, Faculty of Engineering, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Tokyo 184-8588 (Japan), Fax: (+81) 42-388-7295.
authors.forename: Minami
authors.initials: M
authors.lastname: Odagi
authors.forename: Kota
authors.initials: K
authors.lastname: Furukori
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Watanabe
authors.forename: Kazuo
authors.initials: K
authors.lastname: Nagasawa
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*; D006900:Hydroxylation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D044024:Tetralones / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D004952:Esters; D044024:Tetralones; C009423:beta-tetralone; D014508:Urea; D019791:Guanidine; C007164:cumene hydroperoxide
keywords: enantioselectivity; esters; hydroxylation; organocatalysis; oxidation; synthetic methods