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

Seon Mi Kim, Kihang Choi

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)4747-4750
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - 2011 Sep

Keywords

  • Chiral auxiliaries
  • Chirality
  • Enantiomeric purity
  • NMR spectroscopy

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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