Journal of Organic Chemistry p. 4432 - 4439 (1985)
Update date:2022-08-02
Topics:
Baldwin, S. W.
Wilson, J. D.
Aube, J.
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.
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Doi:10.1002/hlca.19860690111
(1986)Doi:10.1016/S0031-9422(00)81963-9
(1980)Doi:10.1021/bi00607a006
(1978)Doi:10.1039/jr9320001215
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(1986)Doi:10.1002/ejoc.201300777
(2013)