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Nature Protocols 3, 215–219 (1 January 2008) | doi:10.1038/nprot.2007.523

Simple protocols for NMR analysis of the enantiomeric purity of chiral diols

Andrew M Kelly , Yolanda P|[eacute]|rez-Fuertes , John S Fossey , Sonia Lozano Yeste , Steven D Bull & Tony D James

A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described here. The present approach involves the derivatization of 1,2- 1,3- and 1,4-diols with 2-formylphenylboronic acid and enantiopure α-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their 1H NMR spectra, thus enabling the determination of the enantiopurity of the parent diol. The protocol as described takes less than 90 min to complete.