Abstract 1,3-Dipolar addition of the nitronic ester (3) to methyl acrylate afforded regiospecifically the isoxzolidine (4), which produced the oxime ether (7) on heating. Reduction of 7 followed by hydrolysis gave the hydroxy amino acid (6), which is known to improve anitibiotic activities. The nitronic ester (3) also reacted regio- and stereospecifically with methyl crotonate to produce the adduct (8). Pyrolysis of (8) followed by reduction and hydrolysis gave the erythro hydroxy amino acid (11).
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Sato et al. (1976) studied this question.
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