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Updated: Jul 5, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Z-Selective Synthesis of Trisubstituted Alkenes by the HWE Reaction Using Modified Still-Gennari Type Reagents
1Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, ul. Sienkiewicza 112, 90-363 Łódź, Poland.
Abstract:
Application of new reagents in the Z-selective synthesis of trisubstituted alkenes via modified Horner-Wadsworth-Emmons carbonyl olefination is presented. The reagents tested are ethyl bis(1,1,1,3,3,3-hexafluoroisopropyl)phosphonoalkanoates, structurally similar to Still-Gennari type reagents. A set of various trisubstituted Z-alkenes was obtained in very high or quantitative yields with excellent Z-selectivity. Remarkably, the procedure was very successful for the synthesis of Z-2-aryl-substituted cinnamic acid esters, maintaining exclusive Z-selectivity even at an increased temperature.
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