New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes

F. Faigl, Sz Deák, Zs Erdélyi, T. Holczbauer, M. Czugler, M. Nyerges, B. Mátravölgyi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Efficient synthesis of several new atropisomeric amino alcohols having 1-phenyl-1H-pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single-crystal X-ray measurement. The consequences of the size of the N-substituents on enantioinduction were examined by employing the enantioselective catalytic addition of diethylzinc to a series of substituted benzaldehydes (yields 91-97%, up to 85% enantiomeric excess). The special effect of the ortho methoxy group of the substrate on the enantioinduction is also interpreted.

Original languageEnglish
Pages (from-to)216-222
Number of pages7
JournalChirality
Volume27
Issue number3
DOIs
Publication statusPublished - 2015

Fingerprint

Benzaldehydes
Amino alcohols
Amino Alcohols
Special effects
Pyrroles
Aldehydes
Skeleton
Ligands
X-Rays
Single crystals
X rays
Substrates
diethylzinc

Keywords

  • Amino alcohol
  • Aromatic aldehyde
  • Asymmetric catalysis
  • Axial chirality
  • Selective hydrolysis

ASJC Scopus subject areas

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

Cite this

New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes. / Faigl, F.; Deák, Sz; Erdélyi, Zs; Holczbauer, T.; Czugler, M.; Nyerges, M.; Mátravölgyi, B.

In: Chirality, Vol. 27, No. 3, 2015, p. 216-222.

Research output: Contribution to journalArticle

Faigl, F, Deák, S, Erdélyi, Z, Holczbauer, T, Czugler, M, Nyerges, M & Mátravölgyi, B 2015, 'New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes', Chirality, vol. 27, no. 3, pp. 216-222. https://doi.org/10.1002/chir.22415
Faigl, F. ; Deák, Sz ; Erdélyi, Zs ; Holczbauer, T. ; Czugler, M. ; Nyerges, M. ; Mátravölgyi, B. / New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes. In: Chirality. 2015 ; Vol. 27, No. 3. pp. 216-222.
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AU - Czugler, M.

AU - Nyerges, M.

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