The tandem Heck-allylic substitution reaction: a novel route to lactams.

[reaction: see text] A novel route to substituted lactams has been developed using a tandem Heck-allylic substitution reaction. The palladium-catalyzed reaction between omega-olefinic N-tosyl amides and vinylic bromides affords in one step the substituted pyrrolidones and piperidones in 49-82% isolated yield. In addition, it is shown that an N-phenyl amide can act as a nucleophile in intramolecular allylic substitution reactions.