title: Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalyzed desymmetrization/kinetic resolution sequence.
abstract: Described herein is the enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination. Two asymmetric reactions (desymmetrization and kinetic resolution) proceeded successively to afford chiral biaryls in excellent enantioselectivities (up to 99% ee). Both experimental and computational studies suggested that this excellent selectivity could be achieved via a highly organized hydrogen bond network among a substrate, a catalyst (chiral phosphoric acid), and a brominating reagent (N-bromophthalimide).
authors: Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
authors: Keiji
authors: K
authors: Mori
authors: Yuki
authors: Y
authors: Ichikawa
authors: Manato
authors: M
authors: Kobayashi
authors: Yukihiro
authors: Y
authors: Shibata
authors: Masahiro
authors: M
authors: Yamanaka
authors: Takahiko
authors: T
authors: Akiyama
mesh_terms: D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D007700:Kinetics; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006841:Hydrocarbons, Aromatic; D010756:Phosphoric Acids; C030242:phosphoric acid