Synthesis and optical resolution of 1‐[(3‐carboxy‐1,1′‐biphenyl)‐2‐yl]‐1H‐pyrrole‐2‐carboxylic acid |
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| Authors: | Ferenc Faigl Bernadett Vas‐Feldhoffer Veronika Kudar Mátyás Czugler Krisztina Pál Miklós Kubinyi |
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| Affiliation: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H‐1111 Budapest, Hungary;2. Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H‐1111 Budapest, Hungary;3. Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H‐1025 Budapest, Hungary;4. Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, 1111 Budapest, Hungary |
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| Abstract: | Site selective mono‐ and dimetalation methods have been developed for the functionalization of 1‐[(1,1′‐biphenyl)‐2‐yl]‐1H‐pyrrole. Optical resolution of the prepared 1‐[(3‐carboxy‐1,1′‐biphenyl)‐2‐yl]pyrrole‐2‐carboxylic acid provided new atropisomeric 1‐arylpyrrole derivatives. The absolute configuration of the pure dicarboxylic acid enantiomers was determined by single crystal X‐ray diffraction and CD spectroscopy. Chirality 2009. © 2009 Wiley‐Liss, Inc. |
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| Keywords: | metalation dilithiation separation of atropisomers absolute configuration CD spectra X‐ray diffraction |
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