4.5 Article

Iron-catalyzed alkenylation of Grignard reagents by enol phosphates

Journal

SYNTHESIS-STUTTGART
Volume -, Issue 16, Pages 2636-2644

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-2008-1067194

Keywords

cross-coupling; Grignard reactions; iron; alkenes; stereoselectivity

Funding

  1. CNRS
  2. Ecole Superieure de Chimie Organique et Minerale (ESCOM)
  3. Fondation de France

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Stereoselective preparation of trisubstituted olefins can be easily performed from an Z/E-mixture of enol phosphates by reacting only the E-isomer with a Grignard reagent in the presence of Fe(acac)(3). This procedure combines a kinetic differentiation and a stereoselective reaction. The coupling is very chemoselective in the presence of an alkyl chloride, an ester, a ketone or a nitrile.

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