Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons

Article abstract of DOI:10.1021/jo00170a037

The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.