The asymmetric Cu(II)-indolinylmethanol complex catalyzed Diels-Alder reaction of 2-vinylindoles with β,γ-unsaturated α-ketoesters: an efficient route to functionalized tetrahydrocarbazoles

Org Biomol Chem. 2014 Jun 28;12(24):4172-6. doi: 10.1039/c4ob00196f.

Abstract

An efficient asymmetric Diels-Alder reaction of 2-vinylindoles with β,γ-unsaturated α-ketoesters has been developed for the construction of functionalized tetrahydrocarbazoles. The products were obtained in high yields (up to 96%) with good stereoselectivities (ee up to 95%, dr up to >99 : 1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Cycloaddition Reaction*
  • Esters / chemistry*
  • Indoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • Carbazoles
  • Esters
  • Indoles
  • Copper
  • 1,2,3,4-tetrahydrocarbazole