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

Research output: Contribution to journal › Article › peer-review

82 Citations (SciVal)

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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ID number: ISI:000237420200003

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

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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journal = "Organic Letters",

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T1 - Simple protocol for NMR analysis of the enantiomeric purity of diols

AU - Kelly, A M

AU - Perez-Fuertes, Y

AU - Arimori, S

AU - Bull, S D

AU - James, T D

N1 - ID number: ISI:000237420200003

PY - 2006

Y1 - 2006

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

SN - 1523-7060

VL - 8

SP - 1971

EP - 1974

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Simple protocol for NMR analysis of the enantiomeric purity of diols

Abstract

Bibliographical note

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