4.8 Article

Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 23, Pages 6567-6571

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703174

Keywords

amides; homogeneous catalysis; Mizoroki-Heck reactions; nickel; quaternary centers

Funding

  1. NIH-NIGMS [R01-GM117016]
  2. Guggenheim Foundation
  3. University of California, Los Angeles
  4. UCLA Graduate Division
  5. Swiss National Science Foundation
  6. NSF [CHE-1048804]
  7. NIH NCRR [S10RR025631]

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We report non-decarbonylative Mizoroki-Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri- and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an adduct bearing vicinal, highly substituted sp3 stereocenters. These results demonstrate that amide derivatives can be used as building blocks for the assembly of complex scaffolds.

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