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Synlett 1998; 1998(8): 879-881
DOI: 10.1055/s-1998-1792
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Regio- and Stereoselective Synthesis of Polyenic Vinyltin Acetals: the Unexpected Effect of the Nature of a Remote Acetal Function on the Regioselectivity of the Stannylmetallation

Franck Suzenet* , Errol Blart, Jean-Paul Quintard
  • *Laboratoire de Synthèse Organique, UMR 6513 du CNRS, Faculté des Sciences et des Techniques de Nantes, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France; Fax (33).2.51.12.54.12; E-mail: quintard@chimie.univ-nantes.fr
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Publication Date:
31 December 2000 (online)

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Stannylmetallation of protected enynals with Bu3Sn(Bu)CuCNLi2 has been proved to be highly dependent on the substrate and on the experimental conditions. (2E,4E)-5-Tributylstannylpenta-2,4-dienal acetal was obtained as a nearly pure isomer when ethylene glycol acetal was used as a protecting group with a 0.28 M stannyl anion concentration.

stannylcupration - enynes - E,E-dienyltin acetals - E,E-dienals

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