Retention of configuration on the oxidative addition of P-H bond to platinum (0) complexes: the first straightforward synthesis of enantiomerically pure P-chiral alkenylphosphinates via palladium-catalyzed stereospecific hydrophosphinylation of alkynes

J Am Chem Soc. 2002 Apr 17;124(15):3842-3. doi: 10.1021/ja025816+.

Abstract

The oxidative addition of pure (R(P))-menthyl phenylphosphinate 1 to a platinum (0) complex proceeds readily with retention of configuration at the chiral phosphorus center which was unambiguously confirmed by an X-ray analysis. In the presence of a catalytic amount of palladium, the hydrophosphinylation of a variety of alkynes with 1 also takes place stereospecifically, with retention of configuration, affording high yields of the corresponding vinylphosphinates bearing a single chirality at phosphorus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Hydrogen / chemistry
  • Molecular Conformation
  • Organoplatinum Compounds / chemical synthesis
  • Organoplatinum Compounds / chemistry*
  • Palladium / chemistry
  • Phosphinic Acids / chemical synthesis*
  • Phosphinic Acids / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Organoplatinum Compounds
  • Phosphinic Acids
  • Palladium
  • Hydrogen