Tandem 1,3-azaprotiocyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone. Remarkable rate enhancement and control of cycloaddition regiochemistry by hafnium(IV) chloride

The tandem 1,3-azaprotiocyclotransfer-cycloaddition reaction between aldoximes and divinyl ketone affords the exo- isomers of substituted 1-aza-8-oxabicyclo[3.2.1]octan-4-ones when a substoichiometric amount of hafnium(iv) chloride is added.

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 20; pp. 2035 - 2036
Main Authors Dunn, PJ, Graham, AB, Grigg, R, Higginson, P
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
EFFICIENT CATALYST
DIPOLAROPHILES
NITRONES
REGIOSELECTIVITY
ACYLATION
TRIFLUOROMETHANESULFONATE
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Summary:The tandem 1,3-azaprotiocyclotransfer-cycloaddition reaction between aldoximes and divinyl ketone affords the exo- isomers of substituted 1-aza-8-oxabicyclo[3.2.1]octan-4-ones when a substoichiometric amount of hafnium(iv) chloride is added.
ISSN:1359-7345
1364-548X
DOI:10.1039/b005389i