|
|||||
|
|
Efficient synthesis of optically active 1-(2-carboxymethyl-6-ethylphenyl)-1H-pyrrole-2-carboxylic acid: a novel atropisomeric 1-arylpyrrole derivative |
|
| Authors: | Ferenc Faigl Bernadett Vas-Feldhoffer Miklós Kubinyi Krisztina Pál Gábor Tárkányi Mátyás Czugler |
| Affiliation: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 8, Hungary;2. Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H-1111 Budapest, Budafoki út 8, Hungary;3. Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budapest, Pusztaszeri út 59-67, Hungary;4. Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, H-1111 Budapest, Budafoki út 8, Hungary |
| 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. |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ | |