Regiochemistry in the Intramolecular Cycloadditions of Substituted 5-Alkenyl and 6-Alkenyl Nitrones

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; Wilson, JD; Aubé, J

Published Date

  • January 1, 1985

Published In

Volume / Issue

  • 50 / 23

Start / End Page

  • 4432 - 4439

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00223a003

Citation Source

  • Scopus