A Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

David A. Tickell; Emma V. Lampard; John P. Lowe; Tony D. James; Steven D. Bull

doi:10.1021/acs.joc.6b01005

A Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

David A. Tickell, Emma V. Lampard, John P. Lowe, Tony D. James, Steven D. Bull

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Abstract

A practically simple derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described. Diols were treated with 0.5 equiv of 1,3-phenyldiboronic acid to afford mixtures of diastereomeric boronate esters whose homochiral/heterochiral ratios are an accurate reflection of the diol’s enantiopurity.

Original language	English
Pages (from-to)	6795–6799
Journal	Journal of Organic Chemistry
Volume	81
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.6b01005
Publication status	Published - 6 Jul 2016

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10.1021/acs.joc.6b01005

JOC Note Diboronic Acid Template
This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see DOI: 10.1021/acs.joc.6b01005
Accepted author manuscript, 485 KB

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abstract = "A practically simple derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described. Diols were treated with 0.5 equiv of 1,3-phenyldiboronic acid to afford mixtures of diastereomeric boronate esters whose homochiral/heterochiral ratios are an accurate reflection of the diol{\textquoteright}s enantiopurity.",

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AU - Lowe, John P.

AU - James, Tony D.

AU - Bull, Steven D.

PY - 2016/7/6

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N2 - A practically simple derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described. Diols were treated with 0.5 equiv of 1,3-phenyldiboronic acid to afford mixtures of diastereomeric boronate esters whose homochiral/heterochiral ratios are an accurate reflection of the diol’s enantiopurity.

AB - A practically simple derivatization protocol for determining the enantiopurity of chiral diols by 1H NMR spectroscopic analysis is described. Diols were treated with 0.5 equiv of 1,3-phenyldiboronic acid to afford mixtures of diastereomeric boronate esters whose homochiral/heterochiral ratios are an accurate reflection of the diol’s enantiopurity.

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JO - Journal of Organic Chemistry

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A Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

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A Simple Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

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A Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

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A Simple Protocol for NMR Analysis of the Enantiomeric Excess of Chiral Diols Using an Achiral Diboronic Acid Template

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