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

doi:10.1016/j.tetasy.2008.01.026

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

Department of Chemistry

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

33 Citations (SciVal)

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 language	English
Pages (from-to)	489-494
Number of pages	6
Journal	Tetrahedron: Asymmetry
Volume	19
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2008.01.026
Publication status	Published - 2008

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ID number: ISI:000255350500014

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10.1016/j.tetasy.2008.01.026

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

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

AU - Kelly, A M

AU - Bull, S D

AU - James, T D

N1 - ID number: ISI:000255350500014

PY - 2008

Y1 - 2008

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.

UR - https://www.scopus.com/pages/publications/39949083373

U2 - 10.1016/j.tetasy.2008.01.026

DO - 10.1016/j.tetasy.2008.01.026

M3 - Article

SN - 0957-4166

VL - 19

SP - 489

EP - 494

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 4

ER -

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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