Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines

Reference:

Perez-Fuertes, Y., Kelly, A. M., Fossey, J. S., Powell, M. E., Bull, S. D. and James, T. D., 2008. Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines. Nature Protocols, 3 (2), pp. 210-214.

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Abstract

A simple three-component chiral derivatization protocol for determining the enantiopurity of chiral primary amines by H-1 NMR spectroscopic analysis is described here. The method involves condensation of the amines with 2-formylphenylboronic acid and enantiopure 1,1'-bi-2-naphthol. This approach affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by the integration of well-resolved diastereotopic resonances in their H-1 NMR spectra, thus enabling the enantiopurity of the parent amine to be determined easily. The protocol, as described, takes less than 90 min to complete.

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