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Updated: Apr 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: efficient access to
Paloma Bernal-Albert1, Hélio Faustino, Ana Gimeno
1Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela , 15782, Santiago de Compostela, Spain.
Abstract:
α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.
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