Highly enantioselective [3+2] coupling of indoles with quinone monoimines promoted by a chiral phosphoric acid

Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10471-5. doi: 10.1002/anie.201405689. Epub 2014 Aug 1.

Abstract

Highly enantioselective [3+2] coupling of 3-substituted indoles with quinone monoimines promoted by a chiral phosphoric acid has been reported. A large variety of benzofuroindolines were prepared in moderate to good yields (up to 98%) with generally excellent enantioselectivities (up to 99% ee).

Keywords: asymmetric catalysis; enantioselectivity; heterocycles; indoles; organocatalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Imines / chemical synthesis
  • Imines / chemistry*
  • Indoles / chemistry*
  • Molecular Conformation
  • Phosphoric Acids / chemistry*
  • Quinones / chemistry*
  • Stereoisomerism

Substances

  • Imines
  • Indoles
  • Phosphoric Acids
  • Quinones
  • phosphoric acid