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

AYDIN A. E.

Tetrahedron Asymmetry, vol.24, no.8, pp.444-448, 2013 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 24 Issue: 8
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetasy.2013.03.011
  • Journal Name: Tetrahedron Asymmetry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.444-448
  • Hatay Mustafa Kemal University Affiliated: Yes

Abstract

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.