Diastereoselective Palladium-Catalyzed Arylcyanation/Heteroarylcyanation of Enantioenriched N-Allylcarboxamides

A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)(2) as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with up to >95:5 dr and with full preseveration of enantioenrichment. By circumventing a difficult nucleophilic cyanation of a hindered neopentyl iodide, this approach represents an improvement to the previously reported formal synthesis of (+)-corynoline.