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Updated: Jul 19, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

アルファ・オメガ・ダイエンの鉄触媒 [2pi + 2pi] サイクル添加: 酸化還元活性サポートリガンドの重要性

Marco W Bouwkamp1, Amanda C Bowman, Emil Lobkovsky

  • 1Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY 14850, USA.

Journal of the American Chemical Society
|October 13, 2006
PubMed
まとめ

鉄の複合体とビス・イミノ・ピリジンのリガンドは, [2pi + 2pi]サイクロアディション反応を効率的に触媒化する. 反応速度は,アミン置換剤のサイズによって影響を受け,調整と製品阻害効果を示す.

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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