Ti(IV)-catalyzed cascade synthesis of tetrahydrofuro[3,2-d]oxazole from arene-1,4-diones

Org Biomol Chem. 2015 Apr 21;13(15):4418-21. doi: 10.1039/c5ob00174a.

Abstract

A tetrahydrofuro[3,2-d]oxazole scaffold was synthesized efficiently and stereoselectively. The tandem ionic hydrogenation, ketalization, and intramolecular cyclization of arene-1,4-diones with a combination of TiCl4/Et3SiH give facile access to tetrahydrofuro[3,2-d]oxazole derivatives in good yields at room temperature.

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrogenation
  • Models, Molecular
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Furans
  • Oxazoles
  • tetrahydro-2-furancarboxylic acid
  • titanium tetrachloride
  • Titanium