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Updated: Jun 12, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids
Chi-Hao Chang1, Chao-Ting Yen1, Théo P Goncalves2
1Department of Applied Chemistry, National University of Kaohsiung 700, Kaohsiung University Road Nanzih District, 81148 Kaohsiung, Taiwan. cmchou@nuk.edu.tw.
Abstract:
A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.
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