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

The tandem 1,3-azaprotiocyclotransfer-cycloaddition reaction between aldoximes and divinyl ketone affords mixtures of exo- and endo-isomers of substituted 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...

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 20; pp. 2033 - 2034
Main Authors Dunn, PJ, Graham, AB, Grigg, R, Higginson, P, Saba, IS
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
POTENTIAL 1,3-DIPOLES
GENERATION
X=Y-ZH SYSTEMS
NITRONES
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Summary:The tandem 1,3-azaprotiocyclotransfer-cycloaddition reaction between aldoximes and divinyl ketone affords mixtures of exo- and endo-isomers of substituted 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 under the thermal reaction conditions.
ISSN:1359-7345
1364-548X
DOI:10.1039/b005393g