Tetrahedron

X= Y–ZH systems as potential 1, 3-dipoles. Part 56: Cascade 1, 3-azaprotio cyclotransfer–cycloaddition reactions between aldoximes and divinyl ketone: the effect of …

…, R Grigg, P Higginson, IS Saba, M Thornton-Pett

Index: Blackwell, Mark; Dunn, Peter J; Graham, Alison B; Grigg, Ronald; Higginson, Paul; Saba, Imaad S; Thornton-Pett, Mark Tetrahedron, 2002 , vol. 58, # 38 p. 7715 - 7725

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Citation Number: 16

Abstract

The cascade 1, 3-azaprotiocyclotransfer (1, 3-APT)-1, 3-dipolar-cycloaddition (1, 3-DC) reaction between aldoximes and divinyl ketone affords mixtures of exo and endo-isomers of substituted 1-aza-7-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.