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

AM Kelly; Y Perez-Fuertes; John S. Fossey; SL Yeste; SD Bull; TD James

doi:10.1038/nprot.2007.523

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

AM Kelly
, Y Perez-Fuertes
, John S. Fossey
, SL Yeste
, SD Bull
, TD James

Chemistry

Research output: Contribution to journal › Article

73 Citations (Scopus)

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 - 1 Jan 2008

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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.",

author = "AM Kelly and Y Perez-Fuertes and Fossey, \{John S.\} and SL Yeste and SD Bull and TD James",

year = "2008",

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doi = "10.1038/nprot.2007.523",

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T1 - Simple protocols for NMR analysis of the enantiomeric purity of chiral diols

AU - Kelly, AM

AU - Perez-Fuertes, Y

AU - Fossey, John S.

AU - Yeste, SL

AU - Bull, SD

AU - James, TD

PY - 2008/1/1

Y1 - 2008/1/1

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.

U2 - 10.1038/nprot.2007.523

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

Abstract

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