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The Tandem Heck-Allylic Substitution Reaction: A Novel Route to Lactams

By Ben L. Feringa, Adriaan J. Minnaard and Pedro Pinho


A novel route to substituted lactams has been developed using a tandem Heck-allylic substitution reaction. The palladium-catalyzed reaction between ω-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.

Year: 2003
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