Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones

Chemistry. 2010 Aug 9;16(30):9117-22. doi: 10.1002/chem.201000568.

Abstract

Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Carbon / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Ligands
  • Molecular Structure
  • Stereoisomerism
  • Zirconium / chemistry*

Substances

  • Hydrocarbons, Fluorinated
  • Indoles
  • Ketones
  • Ligands
  • Carbon
  • Zirconium