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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Hydrazone and Oxime Olefination via Ruthenium Alkylidenes
Daniel J Nasrallah1, Troy E Zehnder1, Jacob R Ludwig1
1Department of Chemistry, University of Michigan, Willard Henry Dow Laboratory, 930 North University Ave., Ann Arbor, MI 48109, USA.
Abstract:
We describe the development of an efficient method for the olefination of hydrazones and oximes. The key design approach that enables this transformation is tuning of the energy/polarity of C=N π-bonds by employing heteroatom functionalities (NR2 , OR). The resulting hydrazones or oximes facilitate olefination with ruthenium alkylidenes. Through this approach, we show that air-stable, commercially available ruthenium alkylidenes provide access to functionalized alkenes (20 examples) in ring-closing reactions with yields up to 88 %.
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