Chemistry letters

Cycloaddition/Ring Opening Sequence of. ALPHA.-Hydroxy Cyclic Nitronates as a Synthetic Equivalent of Functionalized Aliphatic Nitrile Oxides

M Nishiuchi, H Sato, H Ohmura

Index: Nishiuchi, Masaki; Sato, Hiroyasu; Ohmura, Hiroyuki Chemistry Letters, 2008 , vol. 37, # 2 p. 144 - 145

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Citation Number: 2

Abstract

α-Hydroxy cyclic nitronates act as synthetic equivalents of nitrile oxides. Cycloaddition of 3- substituted 4-hydroxy-2-isoxazoline N-oxides or 4-hydroxy-3-hydroxymethyl-2-isoxazoline N- oxides with electron-deficient alkenes produce bicyclic isoxazolidines, which undergo ring opening of one of the ring-fused isoxazolidines on acid treatment to give 2-isoxazoline derivatives by elimination of hydroxyacetaldehyde or carbon–carbon bond cleavage.