A simple and efficient synthesis of optically pure 4-alkylisoxazolidin-4-ols

The reaction between N-hydroxyphthalimide and optically pure epichlorohydrin followed by addition of methanol represents a straightforward procedure for the synthesis of isoxazolidin-4-ols in high enantiomeric purity. Under the same conditions, the reaction of glycidyl arenesulfonates can lead to different products depending on the nature of the sulfonate. This property allowed the synthesis of both enantiomers of 4-methylisoxazolidin-4-ol from the same chiral epoxide starting material.