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Updated: Jul 11, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers
Katherine M Bogle1, David J Hirst, Darren J Dixon
1School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK.
Abstract:
A broadly applicable oxidative coupling strategy of 3-substituted catechols and carbon-centered pro-nucleophiles for the construction of arylated quaternary stereogenic centers has been developed. Pivoting on a base-catalyzed addition of a carbon-centered acid to an in situ generated o-benzoquinone, the method is general and atom-economical and provides remarkably efficient access to one of the most challenging structural motifs. Furthermore, use of chiral bifunctional organocatalysts allows the process to be rendered asymmetric (up to 81% ee).
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