Steric and electronic tuning of atropisomeric amino alcohol type ligands with a 1-arylpyrrole backbone

Szilvia Deák, Béla Mátravölgyi, Gyula Feczku, Zsuzsa Erdélyi, Miklós Nyerges, F. Faigl

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Abstract The synthesis of new, trifluoromethyl group containing atropisomeric amino alcohols and their application in enantioselective diethylzinc additions to aldehydes is described. A significant improvement of the enantioinductive effects of the new ligands by increasing the Brønsted acidity and bulkiness of the triarylcarbinol moiety is also reported. Tuning was achieved by the introduction of phenyl substituents containing two trifluoromethyl groups onto the α-carbon of the tertiary alcohol part of the ligand. The application of the new catalysts provided 1-(substituted phenyl)propanols with excellent enantiomeric purities.

Original languageEnglish
Article number59289
Pages (from-to)593-599
Number of pages7
JournalTetrahedron Asymmetry
Volume26
Issue number10-11
DOIs
Publication statusPublished - May 31 2015

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Amino alcohols
Amino Alcohols
Propanols
alcohols
Tuning
Ligands
tuning
ligands
Propanol
Aldehydes
aldehydes
electronics
Acidity
acidity
purity
Alcohols
Carbon
catalysts
Catalysts
carbon

ASJC Scopus subject areas

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

Cite this

Steric and electronic tuning of atropisomeric amino alcohol type ligands with a 1-arylpyrrole backbone. / Deák, Szilvia; Mátravölgyi, Béla; Feczku, Gyula; Erdélyi, Zsuzsa; Nyerges, Miklós; Faigl, F.

In: Tetrahedron Asymmetry, Vol. 26, No. 10-11, 59289, 31.05.2015, p. 593-599.

Research output: Contribution to journalArticle

Deák, Szilvia ; Mátravölgyi, Béla ; Feczku, Gyula ; Erdélyi, Zsuzsa ; Nyerges, Miklós ; Faigl, F. / Steric and electronic tuning of atropisomeric amino alcohol type ligands with a 1-arylpyrrole backbone. In: Tetrahedron Asymmetry. 2015 ; Vol. 26, No. 10-11. pp. 593-599.
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