Pd-Catalyzed Asymmetric Intramolecular Arylation of α-Keto Amides

Significance

This work describes the Pd-catalyzed enantioselective intramolecular arylation of α-keto anilides which provided access to 3-hydroxy-2-oxindoles with 53-93% yield and 82-99% ee. Poorly accessible derivatives of aliphatic α-keto anilides could also be prepared. Furthermore, the methodology could be expanded to the synthesis of 4-hydroxydihydroquinolinones, which serve as useful building blocks for drug candidates; no easy catalytic asymmetric route to these compounds existed before this work. A putative reaction mechanism was proposed.