Carbenylative Amination with N-Tosylhydrazones

Avinash Khanna, Charles Maung, Kyle R. Johnson, Tom T. Luong and David L. Van Vranken*

*Department of Chemistry, University of California at Irvine, Irvine, California 92697-2025, United States, Email: david.vvuci.edu

A. Khanna, C. Maung, K. R. Johnson, T. T. Luong, D. L. Van Vranken, Org. Lett., 2012, 14, 3233-3235.

DOI: 10.1021/ol301385g

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Abstract

A Pd-catalyzed reaction of vinyl iodides and N-tosylhydrazones assembles η³-allyl ligands through carbene insertion. Intramolecular trapping with nitrogen nucleophiles generates good yields of cinnamyl and pentadienyl amines like those found in alkaloid natural products.

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Key Words

pyrrolidines, piperidines

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ID: J54-Y2012-2040