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

F. Faigl, Béla Mátravölgyi, Tamás Holczbauer, M. Czugler, J. Madarász

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15 Citations (Scopus)

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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Enantiomers
pyrroles
Carboxylic Acids
Carboxylic acids
carboxylic acids
Isomers
Molecular structure
Salts
Single crystals
X ray diffraction
enantiomers
discrimination
molecular structure
isomers
salts
single crystals
diffraction
x rays
2-pyrrolecarboxylic acid
energy

ASJC Scopus subject areas

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

Cite this

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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.",
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T1 - 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

AU - Faigl, F.

AU - Mátravölgyi, Béla

AU - Holczbauer, Tamás

AU - Czugler, M.

AU - Madarász, J.

PY - 2011/11/30

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