Nature Protocols: Simple protocols for NMR analysis of the enantiomeric purity of chiral diols

This Protocol is listed in the following Categories:
Spectroscopy and structural analysis, Synthetic chemistry

Author(s): Andrew M. Kelly, Yolanda Pérez-Fuertes, John S. Fossey, Steven D. Bull and Tony D. James
Affiliation(s): Department of Chemistry, University of Bath
DOI: 10.1038/nprot.2007.523

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

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.

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

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