[reaction: see text] A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by (1)H NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereoisomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.
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Kelly et al. (2006) studied this question.