10.1021/ol048030k.s001
Stéphane Quideau
Stéphane
Quideau
Isabelle Fabre
Isabelle
Fabre
Denis Deffieux
Denis
Deffieux
First Asymmetric Synthesis of
Orthoquinone Monoketal Enantiomers
via Anodic Oxidation
American Chemical Society
2004
First Asymmetric Synthesis
aryl methyl ethers
stereoisomer
Orthoquinone Monoketal Enantiomers
dimethyl ketal unit
utility
chiral ethanol unit
nucleophilic addition reactions
anodic oxidation
synthesis
synthon
orthoquinone monoketals
monohydrolysi
diastereoselective manner
screening
arene
orthoquinone bisketals
attachment point
Anodic Oxidation
2004-11-25 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/First_Asymmetric_Synthesis_of_Orthoquinone_Monoketal_Enantiomers_via_Anodic_Oxidation/3314617
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 <i>pro</i>-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.