817622-26-7Relevant articles and documents
First asymmetric synthesis of orthoquinone monoketal enantiomers via anodic oxidation
Quideau, Stephane,Fabre, Isabelle,Deffieux, Denis
, p. 4571 - 4573 (2007/10/03)
(Chemical equation presented) 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.