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Updated: Sep 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-Catalyzed [2+3] Cycloaddition/Cross-Coupling Reaction: Z/E and Diastereoselective Synthesis of
Xiangyu Tan1, Qianqian Gu1, Xingjiang Yang1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, and School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
Abstract:
Herein, we describe a Pd-catalyzed [2+3] cycloaddition/cross-coupling reaction of allenyl acetates for the Z/E selective and diastereoselective synthesis of dendralene-functionalized dihydrofurans. Remarkably, mechanistic studies show the formation of an epoxide from a carbonyl bond via cycloaddition, which is practically and mechanistically significant for the construction of other bioactive heterocyclic epoxides. This research also revealed the utility and potential of allenic esters as C2 synthons and 1,2-biselectrophiles in cycloaddition reactions.
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