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

Organic Chemistry Frontiers Pub Date: 2021-09-03 DOI: 10.1039/D1QO01147B

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.

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