A practical solvating agent for the chiral NMR discrimination of carboxylic acids

Seon Mi Kim; Kihang Choi

doi:10.1002/ejoc.201100692

A practical solvating agent for the chiral NMR discrimination of carboxylic acids

Seon Mi Kim, Kihang Choi

Department of Chemistry

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

15 Citations (Scopus)

Abstract

A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show ¹H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.

Original language	English
Pages (from-to)	4747-4750
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201100692
Publication status	Published - 2011 Sept

Keywords

Chiral auxiliaries
Chirality
Enantiomeric purity
NMR spectroscopy

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201100692

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AB - A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and (S,S)-1,2-diphenylethylenediamine through a single-step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3-disubstituted structure is crucial for the acid-solvating ability of the bisimidazoline compound.

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KW - Enantiomeric purity

KW - NMR spectroscopy

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A practical solvating agent for the chiral NMR discrimination of carboxylic acids

Abstract

Keywords

ASJC Scopus subject areas

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