title: Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.
abstract: Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3'-Br(2)-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Life Sciences and Engineering Building, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, United States.
authors.forename: Yi
authors.initials: Y
authors.lastname: Luan
authors.forename: Scott E
authors.initials: SE
authors.lastname: Schaus
mesh_terms: D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; D001897:Boronic Acids; D045563:Indolequinones; D010636:Phenols; C068040:quinone methide; C026198:4-methoxydalbergione