Stability of electron deficient activated nitronates under neutral and Lewis acid catalyzed conditions. Facile nitronate cycloaddition reactions to the magnesium …

S Kanemasa, S Kaga, E Wada

Index: Kanemasa, Shuji; Kaga, Shinsuke; Wada, Eiji Tetrahedron Letters, 1998 , vol. 39, # 48 p. 8865 - 8868

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Citation Number: 12

Abstract

N-Methoxy-N-[bis (methoxycarbonyl) methylene] amineN-oxide andN-methoxy-N-( methoxycarbonylmethylene) amineN-oxide as electron-deficient activated nitronates, show an exceptionally high reactivity to the magnesium alkoxides of allylic alcohols. Isoxazolidines or isoxazolines are formed as cycloadducts, depending upon the substitution pattern of the allylic alcohols. When the latter C-monosubstituted nitronate is treated with a ...