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Updated: Sep 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium(0)-Catalyzed Asymmetric Cross Inverse-Electron-Demand Diels-Alder Reaction between Distinct
Ke Xie1, Bao-Rui Kong1, Chuang-Qi Wang1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Abstract:
Here we present an asymmetric and regioselective cross inverse-electron-demand Diels-Alder reaction between 2,4-dienyl carbonyls and 1-heterodienes or allylidenemalononitriles, by reversing the reactivity of the former electrophilic partners via γ,δ-dihapto coordination with palladium(0) and backdonation. A broad spectrum of multifunctional tetrahydropyridines, dihydropyrans and cyclohexene derivatives are generally constructed in high yields, diastereo- and enantioselectivity, even with low catalyst loadings (0.6 mol % of Pd).
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