Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols: New chiral ligands

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An efficient synthetic method has been developed for the preparation of a new family of atropisomeric amino alcohols with 1-phenylpyrrole backbone. The synthesis is based on the different reactivities of the two carboxylic groups in optically active 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2- carboxylic acid (1). The chemical structures of the key intermediates were confirmed by spectroscopic methods and single crystal X-ray diffraction measurements. The very first application of a new optically active amino alcohol as catalyst for the enantioselective addition of diethylzinc to benzaldehyde demonstrated the practical usefulness of atropisomeric compounds in which there are six-atom chains between the two functional groups.

Original languageEnglish
Pages (from-to)532-542
Number of pages11
JournalChirality
Volume24
Issue number7
DOIs
Publication statusPublished - Jul 2012

Fingerprint

Amino alcohols
Amino Alcohols
Ligands
Carboxylic acids
X-Ray Diffraction
Functional groups
Single crystals
X ray diffraction
Atoms
Catalysts
diethylzinc
2-pyrrolecarboxylic acid
benzaldehyde
1H-pyrrole-2-carboxylic acid

Keywords

  • Chiral amino alcohol
  • Enantioselective reaction
  • Metalation
  • Organocatalyst
  • Site selective reaction

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols : New chiral ligands. / Faigl, F.; Mátrav̈olgyi, Beĺa; Szöllösy, A.; Czugler, M.; Tárkányi, G.; Vékey, K.; Kubinyi, M.

In: Chirality, Vol. 24, No. 7, 07.2012, p. 532-542.

Research output: Contribution to journalArticle

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AU - Czugler, M.

AU - Tárkányi, G.

AU - Vékey, K.

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