ol048030k_si_001.pdf (9.02 MB)
First Asymmetric Synthesis of Orthoquinone Monoketal Enantiomers via Anodic Oxidation
journal contribution
posted on 2004-11-25, 00:00 authored by Stéphane Quideau, Isabelle Fabre, Denis DeffieuxAn 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.
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First Asymmetric Synthesisaryl methyl ethersstereoisomerOrthoquinone Monoketal Enantiomersdimethyl ketal unitutilitychiral ethanol unitnucleophilic addition reactionsanodic oxidationsynthesissynthonorthoquinone monoketalsmonohydrolysidiastereoselective mannerscreeningareneorthoquinone bisketalsattachment pointAnodic Oxidation
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