A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

D.A. Tickell; Mary F Mahon; S.D. Bull; T.D. James

doi:10.1021/ol303566k

A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

D.A. Tickell, Mary F Mahon, S.D. Bull, T.D. James

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Abstract

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

Original language	English
Pages (from-to)	860-863
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1021/ol303566k
Publication status	Published - 15 Feb 2013

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abstract = "A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine. ",

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AU - Tickell, D.A.

AU - Mahon, Mary F

AU - Bull, S.D.

AU - James, T.D.

PY - 2013/2/15

Y1 - 2013/2/15

N2 - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

AB - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

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A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

Abstract

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