4.8 Article

Highly Regioselective Intermolecular Hydroacylations of Enamides with Salicylaldehydes

Journal

ORGANIC LETTERS
Volume 13, Issue 15, Pages 3900-3903

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201431c

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Funding

  1. Fonds der Chemischen Industrie
  2. Excellence Initiative of the German federal government
  3. Alexander von Humboldt Foundation
  4. Excellence Initiative of the German state government

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Highly regioselective Intermolecular hydroacylations of enamides under rhodium catalysis with monodentate phosphane ligands are reported for the first time. The presence of MeCN facilitates this novel C-C bond formation, and the electron-deficient phosphine P(p-F-Ph)(3) has proven most effective for the direct hydroacylation of 1-vinyl-2-pyrrolidinone. Accordingly, an atom-economic synthetic route to a-amido ketones from readily available substrates has been developed.

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