Synthesis of novel β-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides

AYDIN A. E.

Tetrahedron Asymmetry, cilt.24, sa.8, ss.444-448, 2013 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24 Sayı: 8
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.tetasy.2013.03.011
  • Dergi Adı: Tetrahedron Asymmetry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.444-448
  • Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

Novel chiral norephedrine-based β-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)2 for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee.© 2013 Elsevier Ltd. All rights reserved.