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Synthesis 1986; 1986(4): 312-315
DOI: 10.1055/s-1986-31595
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Reduction of 4,5-Dihydro-1,2-oxazoles (Δ2-Isoxazolines); A Cycloadditive Approach to 2-Alkenyl Ketones

Dennis P. Curran* , Byeang Hyean Kim
  • *Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 U. S. A.
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Publication Date:
27 September 2002 (online)

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A new cycloadditive route to 2-alkenyl ketones (β,γ-unsaturated ketones) involves: (1) nitrile oxide-allylsilane (or stannane) cycloaddition, (2) reductive cleavage of the resultant isoxazoline, and (3) Peterson elimination. In all cases, the products art: not contaminated by the isomeric 1-alkenyl ketones. Although stereoselectivity in the nitrile oxide cycloaddition to 3-trimethylsilyl-1-butene is low, the resultant diastereomeric cycloadducts can be converted stereospecifically to the corresponding (E)- and (Z)-olefins.