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

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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.
LanguageEnglish
Pages215-219
Number of pages5
JournalNature Protocols
Volume3
Issue number2
DOIs
StatusPublished - 2008

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Esters
Nuclear magnetic resonance
Spectroscopic analysis
1-phenethylamine
2-formylphenylboronic acid

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Simple protocols for NMR analysis of the enantiomeric purity of chiral diols. / Kelly, A M; Perez-Fuertes, Y; Fossey, J S; Yeste, S L; Bull, S D; James, T D.

In: Nature Protocols, Vol. 3, No. 2, 2008, p. 215-219.

Research output: Contribution to journalArticle

Kelly, AM, Perez-Fuertes, Y, Fossey, JS, Yeste, SL, Bull, SD & James, TD 2008, 'Simple protocols for NMR analysis of the enantiomeric purity of chiral diols' Nature Protocols, vol. 3, no. 2, pp. 215-219. DOI: 10.1038/nprot.2007.523
Kelly AM, Perez-Fuertes Y, Fossey JS, Yeste SL, Bull SD, James TD. Simple protocols for NMR analysis of the enantiomeric purity of chiral diols. Nature Protocols. 2008;3(2):215-219. Available from, DOI: 10.1038/nprot.2007.523
Kelly, A M ; Perez-Fuertes, Y ; Fossey, J S ; Yeste, S L ; Bull, S D ; James, T D. / Simple protocols for NMR analysis of the enantiomeric purity of chiral diols. In: Nature Protocols. 2008 ; Vol. 3, No. 2. pp. 215-219
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