A highly efficient and enantioselective synthesis of 3-amino-2-oxindoles through a palladium-catalyzed asymmetric intramolecular arylation of α-ketimino amides using (R)-DiFluorPhos as the coordinating ligand is reported. This report constitutes the first enantioselective palladium-catalyzed arylation of ketimines.

Synthesis of Enantiomerically Enriched 3-Amino-2-oxindoles Through a Palladium-Mediated Asymmetric Intramolecular Arylation of α-Ketimino Amides.-The use of an iodide instead of the triflate leaving group provides only a trace of a racemic product. When R 1 is a heteroaromatic substituent such as indole, no cyclization occurs. The chloride-substituted oxindole (VIII) can be further functionalized via cross-coupling. -(TOLSTOY, P.; LEE, S. X. Y.; SPARR, C.; LEY*, S. V.; Org. Lett. 14 (2012) 18, 4810-4813, http://dx.