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Updated: May 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Unmatched-Electron-Demand Diels-Alder Reaction of Lindenane-Based Electron-Deficient Trienes
Fengxia Yuan1, Zhengsong Huang1, Yan Hao1
1College of Chemistry, Sichuan University, Chengdu 610064, China.
None:
An unmatched-electron-demand Diels-Alder reaction (UMEDDA) between lindenane-based electron-deficient dienes and electron-deficient dienophiles has been developed. The electron-withdrawing group on the dienophile can be extended to ketones, aldehydes, esters, amides, benzoquinones, and glyoxylates, producing [4 + 2] cycloadducts with excellent stereoselectivity and regioselectivity. DFT calculations are conducted to elucidate its regioselectivity, stereoselectivity, and electronic-effect-dependent reactivity. This work contributes to clarifying the generality of UMEDDA reactions and proves the extendable potential of this reaction in the related pharmaceutical research and total synthesis of complex organic molecules.
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