ORGN 244 |
Anodic oxidation of 2-alkoxyphenols and 2-alkoxyphenol ethers into chiral orthoquinone monoketals
| Denis Deffieux, Isabelle Fabre, and Stéphane Quideau. Laboratoire de Chimie des Substances Végétales, Université Bordeaux 1, Centre de Recherche en Chimie Moléculaire, Talence, France |
In the course of our studies to develop novel synthetic methodologies based on the utilization of orthoquinone monoketal synthons, we were interested in the development of convenient procedures for the preparation of chiral orthoquinone monoketal derivatives (e.g., 1). The presence of stereogenic carbon centers in the cyclic ketal group could be exploited to control the stereochemical outcome of reactions at the cyclohexa-2,4-dienone unit. Formation of the desired ketal compounds from readily available 2-alkoxyphenols (e.g., 2) and 2-alkoxyphenol ethers (e.g., 3) was envisaged by anodic oxidation. In contrast to standard chemical ways, such an electrochemical procedure constitutes a mild and environmentally friendly yet powerful way of activating either free arenols or arenol ethers for quinone monoketal formation. The scope and limitations of this methodology will be discussed. |
| |
|
|