Stereoselective Oxindole Synthesis by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Amides

A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.