Simple protocol for NMR analysis of the enantiomeric purity of diols

A M Kelly; Y Perez-Fuertes; S Arimori; S D Bull; T D James

doi:10.1021/ol0602351

Simple protocol for NMR analysis of the enantiomeric purity of diols

A M Kelly, Y Perez-Fuertes, S Arimori, S D Bull, T D James

Department of Chemistry

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63 Citations (Scopus)

Abstract

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.

Original language	English
Pages (from-to)	1971-1974
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol0602351
Publication status	Published - 2006

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Kelly, A. M., Perez-Fuertes, Y., Arimori, S., Bull, S. D., & James, T. D. (2006). Simple protocol for NMR analysis of the enantiomeric purity of diols. Organic Letters, 8(10), 1971-1974. https://doi.org/10.1021/ol0602351

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abstract = "A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.",

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AU - Perez-Fuertes, Y

AU - Arimori, S

AU - Bull, S D

AU - James, T D

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PY - 2006

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N2 - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.

AB - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.

U2 - 10.1021/ol0602351

DO - 10.1021/ol0602351

M3 - Article

VL - 8

SP - 1971

EP - 1974

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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