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

Y Perez-Fuertes, A M Kelly, J S Fossey, M E Powell, S D Bull, T D James

Research output: Contribution to journal › Article

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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.
LanguageEnglish
Pages210-214
Number of pages5
JournalNature Protocols
Volume3
Issue number2
DOIs
StatusPublished - 2008

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Amines
Nuclear magnetic resonance
Spectroscopic analysis
Condensation
Esters
2-formylphenylboronic acid
1,1'-bi-2-naphthol

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

In: Nature Protocols, Vol. 3, No. 2, 2008, p. 210-214.

Research output: Contribution to journal › Article

Perez-Fuertes, Y, Kelly, AM, Fossey, JS, Powell, ME, Bull, SD & James, TD 2008, 'Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines' Nature Protocols, vol. 3, no. 2, pp. 210-214. DOI: 10.1038/nprot.2007.524
Perez-Fuertes Y, Kelly AM, Fossey JS, Powell ME, Bull SD, James TD. Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines. Nature Protocols. 2008;3(2):210-214. Available from, DOI: 10.1038/nprot.2007.524
Perez-Fuertes, Y ; Kelly, A M ; Fossey, J S ; Powell, M E ; Bull, S D ; James, T D. / Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines. In: Nature Protocols. 2008 ; Vol. 3, No. 2. pp. 210-214
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