5-Hydroxy-isoxazolidine: A New Synthetic Approach to a Privileged Heterocycle for Organic Synthesis

A modified pathway towards 5-hydroxy-isoxazolidines has
been preliminarily investigated by taking advantage of the
anti-Markovnikov route in ene reactions of sterically encumbered
nitrosocarbonyl intermediates in the presence of
allylsilylethers. Fluoride-mediated deprotection/cyclization of
the ene adducts afforded the desired heterocycles in quantitative
yields and the methodology is adaptable to a one-pot
procedure.