Preparation of a chiral ferrocenyl derivative containing a biphenyl unit via nickel-mediated homocoupling

Chirality. 2005 May 5;17(4):233-6. doi: 10.1002/chir.20155.

Abstract

Ferrocenyl derivative 2, which possesses a biphenyl unit, was prepared by nickel(0)-mediated homocoupling of a chiral ferrocenyloxazoline. Compound 2 exists as an equilibrium mixture of two diastereomers, in a ratio dependent on temperature and solvent, due to the partially hindered rotation around biaryl bond. Upon complexation with Cu(I) or Zn(II), complete fixation of the stereogenic axis was obtained and a single stable atropoisomer was formed, whose absolute configuration was assigned on the basis of its NOESY spectrum. The 2-Cu(I) complex was used as catalyst in the cyclopropanation of styrene.

MeSH terms

  • Biphenyl Compounds / chemistry*
  • Cyclopropanes / chemistry
  • Ferrous Compounds / chemistry*
  • Ligands
  • Molecular Structure
  • Nickel / chemistry*
  • Stereoisomerism
  • Styrene / chemistry

Substances

  • Biphenyl Compounds
  • Cyclopropanes
  • Ferrous Compounds
  • Ligands
  • diphenyl
  • Styrene
  • Nickel
  • cyclopropane