title: Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.
abstract: A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF(3)·OEt(2). On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
authors.forename: Fenghai
authors.initials: F
authors.lastname: Guo
authors.forename: Leah C
authors.initials: LC
authors.lastname: Konkol
authors.forename: Regan J
authors.initials: RJ
authors.lastname: Thomson
mesh_terms: D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007659:Ketones; D010636:Phenols