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Synlett 1996; 1996(3): 221-224
DOI: 10.1055/s-1996-5377
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Competition between Metallation and Halogen-Lithium Exchange in Halovinylic Acetals

Béatrice Bonnet, Gérard Plé, Lucette Duhamel*
  • *Université de Rouen, URA CNRS DO464 and IRCOF, F 76821 Mont-Saint-Aignan Cedex (FRANCE). Fax: (33)-35-14-66-70
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Publication Date:
31 December 2000 (online)

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Reaction of t-BuLi with haloacetals 1 was studied according to the configuration Z/E, the halogen atom (X=Br, I), the acetal moiety (R=Me, Et) and the solvent (Et2O, THF). While E bromoacetals in Et2O are subject to an exclusive metallation, all other cases yield to an exchange reaction. Diiodoacetal 9a is the precursor of eneacetals 10 and 11 of controlled Z or E configurations.

Enehaloacetals-halogen metal exchange-metallation-precoordination