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Updated: Jun 27, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols
Barry M Trost1, Jia Xie, Nuno Maulide
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Abstract:
A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.
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