Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids

Abstract

Kinetic resolution of [2.2]paracyclophane aldimines was achieved through palladium-catalyzed enantioselective arylation with arylboronic acids. The catalytic process provided reliable access to enantiopure paracyclophane derivatives with planar and central chirality as well as the recovered chiral aldimines with a selectivity factor up to 368. Furthermore, the synthetic utility of the [2.2]paracyclophane aldimines has been demonstrated by converting them into useful chiral building blocks.