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Updated: Nov 23, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes
Laurence N Rohde1, Thérèse H Wild1, Steven T Diver1
1Department of Chemistry, University at Buffalo, the State University of New York, Buffalo, New York 14260, United States.
Abstract:
A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields. The resulting dienes were further transformed by Horner-type Wittig reactions and a Diels-Alder cycloaddition.
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