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Updated: Mar 26, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Gold ((I) -Catalyzed Allenyl Cope Rearrangement: アシンクロニシティからステレオ電子スイッチングによるトラップ可能な中間体への進化

Dinesh V Vidhani1, Marie E Krafft1, Igor V Alabugin1

  • 1Department of Chemistry & Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.

Journal of the American Chemical Society
|February 7, 2016
PubMed
まとめ

この研究は,協調した環周反応を中断するために,ゴールド (I) 触媒を用いた新しい戦略を導入し,新しいカスケード変換を可能にします. 化学者は,電子的および立体電子的要因を制御することで,中断されたCopeの再編成にアクセスできます.

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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