PAPER	Synthesis 2006: 3654-3660   DOI: 10.1055/s-2006-950292
© Georg Thieme Verlag Stuttgart · New York
Mild Zinc-Promoted Horner-Wadsworth-Emmons Reactions of Diprotic Phosphonate Reagents
Douglas J. Schauer, Paul Helquist*
University of Notre Dame, Department of Chemistry and Biochemistry and Walther Cancer Research Center, 251 Nieuwland Science Hall, Notre Dame, IN 46556, USA Fax: +1(547)6316652; e-Mail: phelquis@nd.edu;
Received 8 June 2006

Abstract

We report the development of a mild protocol for the Horner-Wadsworth-Emmons reaction of diprotic phosphonates that makes use of a zinc triflate promoter in the presence of mild tertiary amine bases to produce α,β-unsaturated carboxylic acids and amides.

Key words

olefinations - zinc - amides - carboxylic acids - Horner-Wadsworth-Emmons reactions