Axially chiral P-N ligands for the copper catalyzed beta-borylation of alpha,beta-unsaturated esters

Org Biomol Chem. 2009 Jun 21;7(12):2520-4. doi: 10.1039/b900741e. Epub 2009 Apr 15.

Abstract

The synthesis and resolution of a new axially chiral Quinazolinap ligand are reported. The application of this and other related P-N ligands to the copper catalyzed beta-borylation of alpha,beta-unsaturated esters resulted in conversions of up to 100% and ee values of up to 79%. A diastereomerically pure palladacycle of the new ligand was characterised by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Esters / chemistry*
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Nitrogen / chemistry*
  • Phosphorus / chemistry*
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry
  • Stereoisomerism

Substances

  • Esters
  • Ligands
  • Quinazolines
  • Phosphorus
  • Copper
  • Nitrogen
  • Boron