Efficient synthesis of optically active 1-(2-carboxymethyl-6-ethylphenyl)-1H-pyrrole-2-carboxylic acid: a novel atropisomeric 1-arylpyrrole derivative

Ferenc Faigl, Bernadett Vas-Feldhoffer, Miklós Kubinyi, Krisztina Pál, Gábor Tárkányi, Mátyás Czugler

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

An efficient synthesis and resolution of (±)-1-(2-carboxymethyl-6-ethylphenyl)-1H-pyrrole-2-carboxylic acid has been developed for the preparation of novel optically active atropisomers. The ee values were measured by a 1H NMR spectroscopic method using quinidine as the chiral complexing agent. Absolute configurations of the separated enantiomers were determined using single crystal X-ray diffraction measurements of both the disodium salt and the (R)-1-phenylethylamine salt of the enantiomerically pure dicarboxylic acid, separately. The analysis of the CD spectra with the aid of TD-DFT quantum chemical calculations confirmed the assignment of configurations.

Original languageEnglish
Pages (from-to)98-103
Number of pages6
JournalTetrahedron Asymmetry
Volume20
Issue number1
DOIs
Publication statusPublished - Jan 30 2009

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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