Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: asymmetric synthesis of dihydropyrimidines

J Am Chem Soc. 2005 Nov 30;127(47):16386-7. doi: 10.1021/ja056092f.

Abstract

The highly enantioselective three-component Biginelli condensation catalyzed by a recyclable chiral ytterbium triflate with a novel hexadentate amine phenol ligand containing a pyridyl group has been developed. A wide range of optically active dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with good to excellent enantioselectivities under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Models, Chemical
  • Models, Molecular
  • Pyrimidines / antagonists & inhibitors
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry*
  • Stereoisomerism
  • Thiones / antagonists & inhibitors
  • Ytterbium / chemistry*

Substances

  • Pyrimidines
  • Thiones
  • monastrol
  • Ytterbium