Resolution of 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2- carboxylic acid with methyl (R)-2-phenylglycinate, reciprocal resolution and second order asymmetric transformation

Ferenc Faigl, Béla Mátravölgyi, Tamás Holczbauer, Mátyás Czugler, János Madarász

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Abstract

A novel, highly efficient method has been developed for the separation of the optical isomers of 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2- carboxylic acid with methyl (R)-2-phenylglycinate. The structural aspects of chiral discrimination have been discussed via comparison of the molecular structures and the packing energies of the diastereoisomeric salts determined by single crystal X-ray diffraction measurements. Reciprocal resolution and a new, highly efficient second order asymmetric transformation of racemic methyl 2-phenylglycinate with the pure enantiomer of the previously resolved atropisomeric carboxylic acid are also reported.

Original languageEnglish
Pages (from-to)1879-1884
Number of pages6
JournalTetrahedron Asymmetry
Volume22
Issue number20-22
DOIs
Publication statusPublished - Nov 30 2011

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ASJC Scopus subject areas

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

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