Tetrahedron

X= Y-ZH systems as potential 1, 3-dipoles. Part 32 generation of nitrones from oximes. Tandem Michael addition-1, 3-dipolar cycloaddition reactions. Background and …

R Grigg, F Heaney, S Surendrakumar, WJ Warnock

Index: Grigg; Heaney; Surendrakumar; Warnock Tetrahedron, 1991 , vol. 47, # 25 p. 4477 - 4494

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Citation Number: 33

Abstract

Intermolecular Michael addition of aldoximes and ketoximes to electronegative olefins generates nitrones. The keto nitrones can be trapped in regiospecific intermolecular cycloaddition reactions giving single cycloadducts in good yield. Chemospecific 1: 1: 1 cycloadducts are obtained from ketoximes, monosubstituted electronegative olefins (Michael acceptor) and N-methylmaleimide (dipolarophile), whilst the chemoselectivity of the ...