Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids

J Org Chem. 2010 Sep 3;75(17):6027-30. doi: 10.1021/jo101084t.

Abstract

A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3-enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h(-1)), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrates / chemical synthesis*
  • Butyrates / chemistry
  • Hydrogenation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Butyrates
  • 3-butenoic acid