When Phosphosugars Meet Gold: Synthesis and Catalytic Activities of Phostones and Polyhydroxylated Phosphonite Au(I) Complexes

Molecules. 2015 Nov 27;20(12):21082-93. doi: 10.3390/molecules201219755.

Abstract

The synthesis and characterization of P-chiral phosphonite-, phosphonate- and thiophosphonate-Au(I) complexes are reported. These novel ligands for Au(I) are based on glycomimetic phosphorus scaffolds, obtained from the chiral pool. The catalytic activities of these complexes are shown in the cyclization of allenols and the hydroamination of 2-(2-propynyl)aniline combined with an organocatalyzed reduction to the corresponding 2-phenyl tetrahydroquinoline. All described gold complexes present excellent catalytic activities.

Keywords: P-stereogeny; catalysis; gold catalysis; heterocycles; phosphosugars.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Catalysis
  • Coordination Complexes / chemical synthesis*
  • Cyclization
  • Gold / chemistry*
  • Molecular Structure
  • Organophosphonates / chemistry*
  • Phosphates / chemistry*
  • Phosphorous Acids / chemistry*
  • Stereoisomerism

Substances

  • 2-(2-propynyl)aniline
  • Aniline Compounds
  • Coordination Complexes
  • Organophosphonates
  • Phosphates
  • Phosphorous Acids
  • Gold
  • thiophosphoric acid