Kinetic Resolution of Racemic Amines via Palladium/Chiral Phosphoric Acid-Catalyzed Intramolecular Allylation: Stereodivergent Access to Chiral 1,3-Disubstituted Isoindolines.

This article presents the kinetic resolution (KR) of racemic amines through stereoselective intramolecular allylation with palladium as a catalyst and chiral phosphoric acid as a cocatalyst. The KR reactions have high selectivity factors, producing chiral 1,3-disubstituted isoindolines (DSIs) and recovering enantioenriched amines. Subsequent palladium-catalyzed allylation of the enantioenriched amines, with an achiral Brønsted acid (BA) cocatalyst, yields -DSIs with favorable stereocontrol. Notably, this study is the first to investigate the effect of using a BA catalyst on the diastereodivergence of allylation reactions, suggesting a stereodivergent strategy for accessing all possible stereoisomers of chiral DSIs, relying on a single chiral source.