A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.
Kelly, A. M., Perez-Fuertes, Y., Arimori, S., Bull, S. D., & James, T. D. (2006). Simple protocol for NMR analysis of the enantiomeric purity of diols. Organic Letters, 8(10), 1971-1974. https://doi.org/10.1021/ol0602351