Publications [#231810] of Steven W. Baldwin

Journal Articles

1. Wilson, SWBJD; Aub, J; 233, Regiochemistry in the Intramolecular Cycloadditions of Substituted 5-Alkenyl Nitrones, J. Org. Chem., vol. 50 no. 23 (1985), pp. 4432, American Chemical Society (ACS), ISSN 0022-3263 [doi]
   (last updated on 2026/01/22)

   Abstract:
   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.