Asymmetric C2-C3 cyclopentannulation of the indole ring

J Am Chem Soc. 2009 Feb 18;131(6):2096-7. doi: 10.1021/ja809919t.

Abstract

Chiral nonracemic alkynyl(alkoxy)carbene complexes of tungsten(0) undergo the [3 + 2] cyclization toward alpha-methylindoles and 1,6-dimethyl-1,2,3,4-tetrahydropyridine to provide 2,3-indoline-fused cyclopentenone and 2,3-piperidine-fused cyclopentenone skeletons, respectively, with very high enantiomeric purities (96-99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Cyclopentanes / chemical synthesis*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Piperidines / chemical synthesis*
  • Pyridines / chemistry*
  • Stereoisomerism
  • Tungsten / chemistry

Substances

  • Alkynes
  • Cyclopentanes
  • Indoles
  • Piperidines
  • Pyridines
  • indoline
  • cyclopentenone
  • Tungsten