Synthesis of new, optically active 1-(substituted aryl)pyrrole derivatives via atropisomerism directed diastereoselective metalation

Angelika Thurner, Bernadett Vas-Feldhoffer, Éva Bottka, Tamás Holczbauer, Miklós Nyerges, Ferenc Faigl

Research output: Contribution to journalArticle

Abstract

Axial chirality directed highly diastereoselective formation of a new stereogenic center in the benzylic position of racemic and optically active 1-[2-(carboxymethyl)-6-ethylphenyl]-1H-pyrrole-2-carboxylic acid (4) is reported as the very first example of efficient intramolecular asymmetric induction effect of the atropisomeric 1-phenylpyrrole skeleton containing dicarboxylic acid on the metalation, alkylation reaction sequence. Configuration of a product ((Ra,S)-7a) was determined by single crystal X-ray diffraction measurements. In addition, stereochemical stability of the new, two chirality elements containing compounds was demonstrated by selective, stepwise transformation of the carboxylic groups into ester and amide functions, respectively.

Original languageEnglish
Pages (from-to)80-96
Number of pages17
JournalArkivoc
Volume2015
Issue number4
DOIs
Publication statusPublished - Apr 25 2015

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Keywords

  • Asymmetric induction
  • Atropisomer
  • Chiral 1-phenylpyrroles
  • Diastereoselective metalation
  • Stereoselective alkylation

ASJC Scopus subject areas

  • Organic Chemistry

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