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Org Lett. 2004 Nov 25;6(24):4571-3.

First asymmetric synthesis of orthoquinone monoketal enantiomers via anodic oxidation.

Author information

1
Institut 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].

PMID:
15548078
DOI:
10.1021/ol048030k

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