Chiral Phosphorus-Olefin Ligands for the Rh(I) -Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron-Deficient Olefins

Chem Asian J. 2016 May 20;11(10):1518-22. doi: 10.1002/asia.201600143. Epub 2016 Apr 18.

Abstract

New chiral phosphorus-olefin hybrid ligands derived from the rigid "privileged" l-proline have been conveniently prepared and applied in the rhodium-catalyzed asymmetric arylation of electron-deficient olefins with arylboronic acids at room temperature; this reaction provides the desired products in excellent yields and high enantioselectivities. The origin of observed stereoselectivity has been investigated by density functional theory (DFT) calculations.

Keywords: L-proline; asymmetric arylation; electron-deficient olefins; ligands; rhodium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Boronic Acids / chemistry*
  • Catalysis
  • Cyclohexenes / chemistry*
  • Ligands
  • Organophosphorus Compounds / chemistry*
  • Pyrrolidines / chemistry
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Benzene Derivatives
  • Boronic Acids
  • Cyclohexenes
  • Ligands
  • Organophosphorus Compounds
  • Pyrrolidines
  • Ruthenium