(+)-BINOL and Pure Shift Experiment: A Bidirectional Approach for NMR Chiral Discrimination of Overcrowded Spectra of Primary Amines

In this work, enantiopure 1,1’-bi-2-naphthol (BINOL) derivatives and carboxylic acids were evaluated as chiral solvating agents (CSAs) in the nuclear magnetic resonance (NMR) chiral discrimination of primary amines. Among the CSAs screened, the readily available (+)-BINOL revealed a simple and rapid...

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Bibliographic Details
Published inJournal of the Brazilian Chemical Society Vol. 29; no. 8; pp. 1638 - 1644
Main Authors Merino, Juliana, Keppler, Artur, Silva, Márcio
Format Journal Article
LanguageEnglish
Portuguese
Published Sociedade Brasileira de Química 01.08.2018
Subjects
CHEMISTRY, MULTIDISCIPLINARY
pure shift experiment
NMR chiral discrimination
primary amines
chiral solvating agent
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Summary:In this work, enantiopure 1,1’-bi-2-naphthol (BINOL) derivatives and carboxylic acids were evaluated as chiral solvating agents (CSAs) in the nuclear magnetic resonance (NMR) chiral discrimination of primary amines. Among the CSAs screened, the readily available (+)-BINOL revealed a simple and rapid chiral auxiliary for 1H NMR chiral discrimination. The procedure required few minutes, assigning of the absolute configuration. The protocol was improved using the 1H pure shift pulse sequence for overcrowded alkyl primary amines due to the absence of JHH couplings. The 1H pure shift NMR experiment and the readily available (+)-BINOL chiral auxiliary can be used for routine chiral discrimination analysis of complex NMR spectra.
ISSN:0103-5053
1678-4790
1678-4790
DOI:10.21577/0103-5053.20180035