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Updated: Aug 21, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes
Shona Banjo1, Keisuke Nakata1, Eiko Nakasuji1
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Abstract:
A copper-catalyzed electrophilic enamidation starting from alkynes is reported. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which directly undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. High functional group tolerance of hydrozirconation enables the use of functionalized alkynes including esters. The developed conditions are successfully applied to syntheses of partial structures found in biologically active natural products.
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