Abstract
AbstractA series of 5‐hydroxyisoxazolidines has been successfully synthesized through tris(hydroxymethyl)aminomethane (TRIS) buffered hydroxylamine hydrochloride and α, β‐ unsaturated ketones reaction. This synthetic approach can be considered as environmentally friendly because of the use of non‐toxic and non‐hazardous reagents at room temperature. The reaction is also metal‐free and generates minimum non‐toxic waste. The structure of 5‐hydroxyisoxazolidines was confirmed not only by extended NMR analysis but by a series of elimination and acetylation reactions. Hydroisoxazolidines are obtained as a mixture of diastereomers (cis‐, trans‐ and N‐invertomers). Usually, three sets of 1HNMR signals are observed for that class of compound (especially for protons H3 and both H4). The analysis of cis‐ and trans‐isomerization of the product 2 b has been conducted.
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