title: Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.
abstract: Chiral diols and biphenols catalyze the multicomponent condensation reaction of phenols, aldehydes, and alkenyl or aryl boronates. The condensation products are formed in good yields and enantioselectivities. The reaction proceeds via an initial Friedel-Crafts alkylation of the aldehyde and phenol to yield an ortho-quinone methide that undergoes an enantioselective boronate addition. A cyclization pathway was discovered while exploring the scope of the reaction that provides access to chiral 2,4-diaryl chroman products, the core of which is a structural motif found in natural products.
authors.affiliation: Center for Molecular Discovery, Boston University , 24 Cummington Mall, Boston, Massachusetts 02215, United States.
authors.forename: Keith S
authors.initials: KS
authors.lastname: Barbato
authors.affiliation: Center for Molecular Discovery, Boston University , 24 Cummington Mall, Boston, Massachusetts 02215, United States.
authors.forename: Yi
authors.initials: Y
authors.lastname: Luan
authors.affiliation: Center for Molecular Discovery, Boston University , 24 Cummington Mall, Boston, Massachusetts 02215, United States.
authors.forename: Daniele
authors.initials: D
authors.lastname: Ramella
authors.affiliation: Center for Molecular Discovery, Boston University , 24 Cummington Mall, Boston, Massachusetts 02215, United States.
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
authors.affiliation: Center for Molecular Discovery, Boston University , 24 Cummington Mall, Boston, Massachusetts 02215, United States.
authors.forename: Scott E
authors.initials: SE
authors.lastname: Schaus
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D001688:Biological Products / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D045563:Indolequinones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001688:Biological Products; D001897:Boronic Acids; D002839:Chromans; D045563:Indolequinones; D010636:Phenols; C068040:quinone methide