Highly enantioselective construction of axial chirality by palladium-catalyzed cycloisomerization of N-alkenyl arylethynylamides

Org Lett. 2009 Apr 16;11(8):1805-8. doi: 10.1021/ol900373z.

Abstract

A cationic palladium(II)/(S)-xyl-Segphos complex catalyzes enantioselective cycloisomerizations of N-alkenyl arylethynylamides leading to axially chiral 4-aryl-2-pyridones in high yields with high ee values. The present catalysis represents the first enantioselective construction of axial chirality by the transition-metal-catalyzed cycloisomerization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Molecular Structure
  • Palladium / chemistry*
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Pyridones
  • Palladium