title: First asymmetric synthesis of orthoquinone monoketal enantiomers via anodic oxidation.
abstract: An asymmetric synthesis of orthoquinone monoketals was accomplished using anodic oxidation to convert aryl methyl ethers bearing a chiral ethanol unit into orthoquinone bisketals, followed by monohydrolysis of their dimethyl ketal unit. All four possible stereoisomers were generated in a diastereoselective manner by varying the attachment point of the chiral pro-ketal alcoholic auxiliary to the starting arene. A preliminary screening of subsequent nucleophilic addition reactions confirmed the potential utility of these synthons in asymmetric synthesis. [reaction: see text]
authors.affiliation: Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France. s.quideau@iecb.u-bordeaux.fr
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
authors.forename: Isabelle
authors.initials: I
authors.lastname: Fabre
authors.forename: Denis
authors.initials: D
authors.lastname: Deffieux