Enantioselective synthesis of chiral alpha-aryl or alpha-alkyl substituted ethylphosphonates via Rh-catalyzed asymmetric hydrogenation with a P-stereogenic BoPhoz-type ligand

J Org Chem. 2009 Jun 5;74(11):4408-10. doi: 10.1021/jo900417m.

Abstract

An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding alpha,beta-unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Ligands
  • Organophosphonates / chemical synthesis*
  • Organophosphorus Compounds / chemical synthesis*
  • Rhodium
  • Stereoisomerism

Substances

  • Ligands
  • Organophosphonates
  • Organophosphorus Compounds
  • Rhodium