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Synlett 1998; 1998(8): 839-840
DOI: 10.1055/s-1998-1787
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A Stereoselective Access to Functional Dienes Containing a Trifluoromethyl Group via Stille Cross Coupling of Ethyl 4,4,4-Trifluoro-3-iodobutenoate

Gildas Prié* , Jerôme Thibonnet, Mohamed Abarbri, Alain Duchêne, Jean-Luc Parrain
  • *Laboratoire de Physicochimie des Interfaces et des Milieux Réactionelles, Faculté des Sciences de Tours, Parc de Grandmont, F-37200 Tours, France; Fax 33 2 47 36 69 59; E-mail: duchene@delphi.phys.univ-tours.fr
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Publication Date:
31 December 2000 (online)

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Stereoselective construction of 3-trifluoromethyl conjugated dienoates or enynoates was achieved from ethyl (Z)-4,4,4-trifluoro-3-iodobutenoate and alkenyltin or alkynyltin reagents through the Stille reaction. Reduction of ethyl 3-trifluoromethyldienoates using DIBAL-H selectively afforded allylic alcohols.

conjugated 3-trifluoromethyl dienoates or dienols - Stille cross-coupling reaction - vinyltin reagents - vinylic iodide - substitution - reduction