Design and Synthesis of Pyrrolidinyl Ferrocene-Containing Ligands and Their Application in Highly Enantioselective Rhodium-Catalyzed Olefin Hydrogenation

Molecules. 2022 Sep 17;27(18):6078. doi: 10.3390/molecules27186078.

Abstract

Herein, we report the design and synthesis of a series of chiral pyrrolidine-substituted ferrocene-derived ligands. The proficiency of this novel structural motif was demonstrated in the Rh-catalyzed asymmetric hydrogenation of dehydroamino acid esters and α-aryl enamides. The products were obtained with full conversions and excellent levels of enantioselectivities of up to >99.9% ee and 97.7% ee, respectively, using a BINOL-substituted phosphine-phosphoaramidite ligand which possesses planar, central, and axial chirality elements.

Keywords: asymmetric catalysis; chiral ligand; ferrocene; rhodium-catalyzed olefin reduction.

MeSH terms

  • Alkenes
  • Catalysis
  • Ferrous Compounds
  • Hydrogenation
  • Ligands
  • Metallocenes
  • Pyrrolidines
  • Rhodium* / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Ferrous Compounds
  • Ligands
  • Metallocenes
  • Pyrrolidines
  • Rhodium
  • ferrocene