An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers

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).