Rh(I)-Catalyzed Asymmetric Synthesis of 3-Substituted Isoindolinones through CO Gas-Free Aminocarbonylation

Abstract

A highly efficient and accessible synthesis of chiral 3-substituted isoindolinone frameworks is described. The synthesis involved the Rh­(I)-catalyzed asymmetric arylation of boronic acids to 2-halobenzaldimines and the subsequent Rh­(I)-catalyzed intramolecular aminocarbonylation of the resulting 2-halobenzylamines using an aldehyde as the carbonyl source. The method tolerates a variety of functional groups, yielding isoindolinone derivatives in moderate to high yields with high ee-values. In addition, two Rh­(I)-catalyzed transformations could be efficiently accomplished in a one-pot sequence to give chiral isoindolinones by the simple addition of a ligand and an aldehyde after the Rh­(I)-catalyzed asymmetric arylation