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

A M Kelly; Y Perez-Fuertes; J S Fossey; S L Yeste; S D Bull; T D James

doi:10.1038/nprot.2007.523

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

A M Kelly, Y Perez-Fuertes, J S Fossey, S L Yeste, S D Bull, T D James

Department of Chemistry

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93 Citations (SciVal)

Abstract

A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by H-1 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 alpha-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their H-1 NMR spectra, thus enabling the determination of the enantiopurity of the parent diol. The protocol as described takes less than 90 min to complete.

Original language	English
Pages (from-to)	215-219
Number of pages	5
Journal	Nature Protocols
Volume	3
Issue number	2
DOIs	https://doi.org/10.1038/nprot.2007.523
Publication status	Published - 2008

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ID number: ISI:000254137000008

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10.1038/nprot.2007.523

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title = "Simple protocols for NMR analysis of the enantiomeric purity of chiral diols",

abstract = "A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by H-1 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 alpha-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their H-1 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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T1 - Simple protocols for NMR analysis of the enantiomeric purity of chiral diols

AU - Kelly, A M

AU - Perez-Fuertes, Y

AU - Fossey, J S

AU - Yeste, S L

AU - Bull, S D

AU - James, T D

N1 - ID number: ISI:000254137000008

PY - 2008

Y1 - 2008

N2 - A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by H-1 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 alpha-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their H-1 NMR spectra, thus enabling the determination of the enantiopurity of the parent diol. The protocol as described takes less than 90 min to complete.

AB - A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by H-1 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 alpha-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their H-1 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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DO - 10.1038/nprot.2007.523

M3 - Article

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VL - 3

SP - 215

EP - 219

JO - Nature Protocols

JF - Nature Protocols

IS - 2

ER -

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

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