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Updated: Jul 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-catalyzed reactions of β-alkoxy/phenoxy enones with dimethyl diazomalonate
1Department of Chemistry, Faculty of Science and Letters, İstanbul Technical University, İstanbul, Turkey.
Abstract:
2,3-dihydrofurans were synthesized from carbonyl-ylides via 1,5-electrocyclization reactions with high yields. Dimethyl diazomalonate was reacted with several β-alkoxy and/or β-phenoxy α,β-unsaturated compounds in the presence of Cu(acac)2 as a catalyst. From the reaction of β-methoxy enone with diazo compound, dioxole, and Cα-H insertion products were also obtained as side products along with 2,3-dihydrofuran derivative. When the unsaturated compound has an ester and a ketone group, only one dihydrofuran derivative was formed, which occurred by the 1,5-ring closure of keto-carbonyl ylide. Dihydrofuran derivative from the formation of ester carbonyl ylide in the reactions was not obtained.
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