Tandem 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone. The effect of oxime E/Z-isomerism on cycloaddition stereoselectivity

Authors
Dunn, PJ Graham, AB Grigg, R Higginson, P Saba, IS
Citation
Pj. Dunn et al., Tandem 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone. The effect of oxime E/Z-isomerism on cycloaddition stereoselectivity, CHEM COMMUN, (20), 2000, pp. 2033-2034
Citations number
4
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
20
Year of publication
2000
Pages
2033 - 2034
Database
ISI
SICI code
1359-7345(2000):20<2033:T1CRBA>2.0.ZU;2-E
Abstract
The tandem 1,3-azaprotiocyclotransfer-cycloaddition reaction between aldoxi mes and divinyl ketone affords mixtures of exo- and endo-isomers of substit uted 1-aza-8-oxabicyclo[3.2.1]octan-4-ones, the ratio of which is dependent on the E/Z geometry of the starting oxime and its ability to isomerise und er the thermal reaction conditions.