A new pyrrolidine-derived atropisomeric amino alcohol as a highly efficient chiral ligand for the asymmetric addition of diethylzinc to aldehydes

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

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A highly efficient pyrrolidine-derived atropisomeric amino alcohol, (Sa)-1-[2-diphenylhydroxymethyl-6-(trifluoromethyl)phenyl]-2-(1-pyrrolido)methyl-1H-pyrrole, has been synthesized as a chiral ligand for the enantioselective addition of diethylzinc to some prochiral aldehydes to afford (S)-alcohols. The conversion rates were close to quantitative with good to excellent enantiomeric excesses (up to 95% ee).

Original languageEnglish
Pages (from-to)6891-6894
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number50
DOIs
Publication statusPublished - Dec 10 2014

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Amino Alcohols
Pyrroles
Aldehydes
Alcohols
Ligands
pyrrolidine
diethylzinc

Keywords

  • Amino alcohol
  • Asymmetric catalysis
  • Axial chirality
  • Chiral ligand
  • Enantioselective addition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A new pyrrolidine-derived atropisomeric amino alcohol as a highly efficient chiral ligand for the asymmetric addition of diethylzinc to aldehydes. / Faigl, F.; Erdélyi, Zsuzsa; Deák, Szilvia; Nyerges, Miklós; Mátravölgyi, Béla.

In: Tetrahedron Letters, Vol. 55, No. 50, 10.12.2014, p. 6891-6894.

Research output: Contribution to journalArticle

Faigl, F. ; Erdélyi, Zsuzsa ; Deák, Szilvia ; Nyerges, Miklós ; Mátravölgyi, Béla. / A new pyrrolidine-derived atropisomeric amino alcohol as a highly efficient chiral ligand for the asymmetric addition of diethylzinc to aldehydes. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 50. pp. 6891-6894.
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AU - Nyerges, Miklós

AU - Mátravölgyi, Béla

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