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The reaction of N-benzyl-C-(alkoxymethyl) nitrones with lithium and sodium enolates derived from menthyl and bornyl acetates affords mixtures of hydroxylamines and isoxazolidin-5-ones. On the other hand, the reaction with the silyl ketene acetals prepared from the above-mentioned acetates mainly affords the silylated hydroxylamines. In both cases the crude reaction mixtures can be smoothly transformed into enantioenriched mixtures of 3-(alkoxymethyl) isoxazolidin-5- ones which are key intermediates in the synthesis of isoxazolidinyl nucleosides.

Nucleophilic additions of chiral non-racemic enolates to N-benzyl-C-(alkoxymethyl) nitrones