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Updated: May 24, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Fe-catalyzed allylic C-C-bond activation: vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic
André P Dieskau1, Michael S Holzwarth, Bernd Plietker
1Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, DE-70569 Stuttgart, Germany.
Abstract:
The low-valent iron complex Bu(4)N[Fe(CO)(3)(NO)] (TBAFe) catalyzes the allylic C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.
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