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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
First asymmetric synthesis of orthoquinone monoketal enantiomers via anodic oxidation
Stéphane Quideau1, Isabelle Fabre, Denis Deffieux
1Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France. s.quideau@iecb.u-bordeaux.fr
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]
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