Enantioselective Rh-catalyzed hydrogenation of 3-aryl-2-phosphonomethylpropenoates by a new class of chiral ferrocenyl diphosphine ligands

Org Lett. 2009 Aug 6;11(15):3226-9. doi: 10.1021/ol9012469.

Abstract

A new class of chiral ferrocenyl diphosphine ligands with an imidazole ring, (R(c),S(Fc))-ImiFerroPhos, has been prepared from acylferrocenes through a five-step transformation and successfully applied in the Rh-catalyzed asymmetric hydrogenation of various 3-aryl-substituted 2-phosphonomethylpropenoates, in which a series of chiral 3-phosphono-2-arylmethylpropanoic acid derivatives were achieved in ee values of up to 98%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Hydrogenation
  • Imidazoles / chemistry*
  • Ligands
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Imidazoles
  • Ligands
  • Organophosphonates
  • Rhodium