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

Aydın A. E., Yüksekdanacı S.

TETRAHEDRON ASYMMETRY, vol.24, pp.14-22, 2013 (SCI-Expanded)

  • Publication Type: Article / Article
  • Volume: 24
  • Publication Date: 2013
  • Journal Name: TETRAHEDRON ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED)
  • Page Numbers: pp.14-22
  • Hatay Mustafa Kemal 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

b-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

b-nitroalkanol for p-nitrobenzaldehyde.