All articles of this category 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.
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Curran et al. (1986) studied this question.