Regiochemistry in the Intramolecular Cycloadditions of Substituted 5-Alkenyl and 6-Alkenyl Nitrones
A series of 5-alkenyl and 6-alkenyl aldehydes bearing aryl and ester functionality on the alkene and with and without 1, 3-dioxolane substitution at the 3 position has been prepared. The N-methyl and N-benzyl nitrones derived by the condensation of the aldehydes with the corresponding hydroxylamines undergo intramolecular 1, 3-dipolar cycloaddition on heating (or at room temperature in two instances) to give either bridged or fused isoxazolidines depending on the regiochemistry of the cycloaddition reaction. The 6-alkenyl nitrones give fused products in all cases except those bearing an aryl group at C-6, which give bridged products. All of the 5-alkenyl nitrones prepared in this study cyclized to afford fused isoxazolidines. © 1985, American Chemical Society. All rights reserved.
Baldwin, SW; Wilson, JD; Aubé, J
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