title: Diastereo- and enantioselective direct catalytic aldol reaction of 2-hydroxyacetophenones with aldehydes promoted by a heteropolymetallic complex: catalytic asymmetric synthesis of anti-1,2-diols.
abstract: An anti-selective direct catalytic asymmetric aldol reaction of 2-hydroxyacetophenones with aldehydes is described. The reaction is catalyzed by a heteropolymetallic complex to afford anti-alpha,beta-dihydroxy ketones as the major diastereomer with excellent enantioselectivity. The use of 2-hydroxyacetophenones bearing electron-donating groups at the phenyl moiety enabled efficient transformation of the aldol products (alpha,beta-dihydroxy ketones) into the corresponding alpha,beta-dihydroxy ester derivatives via Baeyer-Villiger oxidation. A plausible reaction mechanism is also discussed based on the stereochemistry of the products.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Yoshikawa
authors.forename: Takeyuki
authors.initials: T
authors.lastname: Suzuki
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki