Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands

Ebru Aydin A., Yuksekdanaci S.

Tetrahedron Asymmetry, vol.24, no.1, pp.14-22, 2013 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 24 Issue: 1
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetasy.2012.11.022
  • Journal Name: Tetrahedron Asymmetry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.14-22
  • Uşak University Affiliated: No

Abstract

Chiral oxazolines have been synthesized from norephedrine and pyrrole nitrile or benzoyl chloride and applied to the catalytic asymmetric Henry reactions of p-nitro aldehydes with nitromethane to provide β-hydroxy nitroalkanols in high conversion (up to 92%). The reaction was then optimized in terms of the metal, solvent, temperature, and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and isopropanol as the solvent gave the best enantioselectivities (up to 84% ee) of the corresponding β-nitroalkanol for p-nitrobenzaldehyde. © 2012 Elsevier Ltd. All rights reserved.