Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction

AYDIN A. E.

Applied Organometallic Chemistry, cilt.27, sa.5, ss.283-289, 2013 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 5
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1002/aoc.2969
  • Dergi Adı: Applied Organometallic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.283-289
  • Anahtar Kelimeler: chiral amino alcohols, copper complex, enantioselective synthesis, Henry reaction, thiolated amino alcohols
  • Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl- or ethyl-substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide β-hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and 2-propanol as the solvent provided the best enantioselectivities (up to 96% ee) of the corresponding nitroalcohols for aliphatic aldehydes. Copyright © 2013 John Wiley & Sons, Ltd. Chiral thiophene contanining amino alcohol ligands were synthesized from norephedrine and substituted 5-thiophene-2-carbaldehyde. This novel chiral ligands were used to catalyze enantioselective Henry reaction of various aldehydes and nitroalkanes in high yields with good to high enantio- and diastereoselectivities. Copyright © 2013 John Wiley & Sons, Ltd.