Atroposelective carbonylation of aryl iodides with amides: facile synthesis of enantioenriched cyclic and acyclic amides

Abstract

Axially chiral cyclic and acyclic amides are frequently found in natural products and bioactive molecules, but catalytic asymmetric synthesis of these atropisomers with high efficiency has been a formidable challenge. We herein describe an unprecedented palladium-catalyzed asymmetric carbonylation of ArI with carbon monoxide (CO) to atroposelectively expand a class of 2-arylisoindoline-1,3-diones and N-acetyl-N-phenyl benzamides in good yields with high enantioselectivities, which represents the first example that inlays the carbonyl group in the axially chiral amides via a carbonylative reaction. Besides, a pair of enantiomorphous isomers of 2-arylisoindoline-1,3-diones can be elegantly obtained by controlling substituents at different positions.