Simple chiral derivatisation protocols for NMR analysis of the enantiopurity of 1,2-diphenylethane-1,2-diamine and N-Boccyclohexane-1,2-diamine

A M Kelly, S D Bull, T D James

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26 Citations (Scopus)

Abstract

Practically simple three-component chiral derivatisation protocols for determining the enantiopurity of vicinal C-2-symmetric diamines by H-1 NMR spectroscopic analysis are described. This involves the treatment of 1,2-diphenylethane-1,2-diamine or N-Boccyclohexane-1,2-diamine with 2-formylphenylboronic acid and enantiopure BINOL, which afford mixtures of diastereoisomeric boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diamine. (C) 2008 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)489-494
Number of pages6
JournalTetrahedron: Asymmetry
Volume19
Issue number4
DOIs
Publication statusPublished - 2008

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Diamines
Spectroscopic analysis
diamines
Esters
Nuclear magnetic resonance
nuclear magnetic resonance
Acids
spectroscopic analysis
esters
acids
1,2-dihydrostilbene

Cite this

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abstract = "Practically simple three-component chiral derivatisation protocols for determining the enantiopurity of vicinal C-2-symmetric diamines by H-1 NMR spectroscopic analysis are described. This involves the treatment of 1,2-diphenylethane-1,2-diamine or N-Boccyclohexane-1,2-diamine with 2-formylphenylboronic acid and enantiopure BINOL, which afford mixtures of diastereoisomeric boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diamine. (C) 2008 Elsevier Ltd. All rights reserved.",
author = "Kelly, {A M} and Bull, {S D} and James, {T D}",
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T1 - Simple chiral derivatisation protocols for NMR analysis of the enantiopurity of 1,2-diphenylethane-1,2-diamine and N-Boccyclohexane-1,2-diamine

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AU - Bull, S D

AU - James, T D

N1 - ID number: ISI:000255350500014

PY - 2008

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N2 - Practically simple three-component chiral derivatisation protocols for determining the enantiopurity of vicinal C-2-symmetric diamines by H-1 NMR spectroscopic analysis are described. This involves the treatment of 1,2-diphenylethane-1,2-diamine or N-Boccyclohexane-1,2-diamine with 2-formylphenylboronic acid and enantiopure BINOL, which afford mixtures of diastereoisomeric boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diamine. (C) 2008 Elsevier Ltd. All rights reserved.

AB - Practically simple three-component chiral derivatisation protocols for determining the enantiopurity of vicinal C-2-symmetric diamines by H-1 NMR spectroscopic analysis are described. This involves the treatment of 1,2-diphenylethane-1,2-diamine or N-Boccyclohexane-1,2-diamine with 2-formylphenylboronic acid and enantiopure BINOL, which afford mixtures of diastereoisomeric boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diamine. (C) 2008 Elsevier Ltd. All rights reserved.

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JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

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