Cinchona alkaloid derived ligands in catalytic asymmetric transfer hydrogenation

Org Biomol Chem. 2003 Jul 21;1(14):2522-6. doi: 10.1039/b304060g.

Abstract

A collection of chiral quinuclidine ligands, derived from the Cinchona alkaloids quinine and quinidine, has been evaluated in the catalytic asymmetric transfer hydrogenation of aromatic ketones. It was fond that [IrCl(COD)]2 complexes of the diamines QCI-Amine and QCD-Amine gave the most active catalysts, capable of reducing a range of aromatic ketones with excellent conversions and good enantioselectivities (up to 95% ee). These are the best selectivities reported for ligands based on the quinuclidine core in an asymmetric transformation, and advocate that these ligands, commercially available in both pseudo-enantiomeric forms, will find practical use in this and other catalytic processes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Hydrogenation
  • Ketones / chemistry
  • Quinuclidines / chemistry
  • Stereoisomerism

Substances

  • Cinchona Alkaloids
  • Ketones
  • Quinuclidines