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

AYDIN A. E.

Russian Journal of Organic Chemistry, cilt.56, sa.5, ss.901-909, 2020 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 56 Sayı: 5
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1134/s1070428020050255
  • Dergi Adı: Russian Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.901-909
  • Anahtar Kelimeler: 1,2-addition, chiral amino alcohols, enantioselective synthesis, thiolated amino-alcohols
  • Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

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.