Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

AYDIN A. E.

Russian Journal of Organic Chemistry, vol.56, no.5, pp.901-909, 2020 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 56 Issue: 5
  • Publication Date: 2020
  • Doi Number: 10.1134/s1070428020050255
  • Journal Name: Russian Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Page Numbers: pp.901-909
  • Keywords: 1,2-addition, chiral amino alcohols, enantioselective synthesis, thiolated amino-alcohols
  • Hatay Mustafa Kemal University Affiliated: Yes

Abstract

Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.