Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate

Org Lett. 2014 Jul 3;16(13):3480-3. doi: 10.1021/ol501409a. Epub 2014 Jun 25.

Abstract

We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkynes / chemistry*
  • Carbonates / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Palladium / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Tryptamines / chemistry*

Substances

  • Alkynes
  • Carbonates
  • Indoles
  • Spiro Compounds
  • Tryptamines
  • Palladium