Trapping of Transient Zwitterionic Intermediates by N-Acylpyridinium Salts: A Palladium-Catalyzed Diastereoselective Three-Component Reaction.

We developed a palladium-catalyzed diastereoselective three-component reaction of N-aryl diazoamides, pyridine, and chloroformate, which proceeded through trapping of transient zwitterionic intermediates by in situ formed N-acylpyridinium salts in a regioselective 1,4-addition fashion. This reaction can rapidly provide a library of biologically relevant 4-(2-oxoindolin-3-yl)-1,4-dihydropyridine derivatives in high yields (up to 98%) with moderate to excellent diastereoselectivities (up to >95:5 dr) under mild reaction conditions.