X=Y–ZH systems as potential 1,3-dipoles. Part 57: Cascade 1,3-azaprotio cyclotransfer–cycloaddition reactions between aldoximes and divinyl ketone: remarkable rate enhancement and control of cycloaddition regiochemistry by Lewis acids

Peter J Dunn,Alison B Graham,Ronald Grigg,Paul Higginson,Mark Thornton-Pett

doi:10.1016/s0040-4020(02)00836-0

X=Y–ZH systems as potential 1,3-dipoles. Part 57: Cascade 1,3-azaprotio cyclotransfer–cycloaddition reactions between aldoximes and divinyl ketone: remarkable rate enhancement and control of cycloaddition regiochemistry by Lewis acids

Peter J Dunn, Alison B Graham + Show 3 more

https://doi.org/10.1016/s0040-4020(02)00836-0

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Journal: Tetrahedron	Publication Date: Sep 1, 2002
Citations: 11

Affiliation: Pfizer (United Kingdom), University of Leeds

#Remarkable Rate Enhancement #ZH Systems + Show 8 more

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Abstract

The tandem 1,3-azaprotio cyclotransfer–cycloaddition reaction between aldoximes and divinyl ketone affords the exo-isomers of substituted 1-aza-7-oxabicyclo[3.2.1]octan-4-ones when a substoichiometric amount of hafnium(IV) chloride, zirconium(IV) chloride or aluminium(III) chloride is added.

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