Two practically simple chiral derivatization protocols for determining the enantiopurity of chiral diols by (1)H NMR and (19)F NMR spectroscopic analysis are described, involving treatment of the diol with 2-formylphenylboronic acid and alpha-methyl-4-fluorobenzylamine, or its derivatization with 4-fluoro-2-formylphenylboronic acid and alpha-methyl-benzylamine. Both approaches afford mixtures of imino-boronate esters whose diastereomeric ratio may be measured by (1)H NMR or (19)F NMR spectroscopy, the value of which is an accurate reflection of the enantiopurity of the parent diol.