Stereocontrolled Synthesis of 3-(Ethoxycarbonyl)-4-hydroxy-2-isoxazoline 2-Oxides. A New Approach to the Synthesis of 4-Hydroxylated 2-Isoxazolines

Article abstract of DOI:10.1021/jo00022a005

Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of trans and cis 4-hydroxylated 2-isoxazolines in a predictable way.