An enantioselective approach to highly substituted tetrahydrocarbazoles through hydrogen bonding-catalyzed cascade reactions

Org Lett. 2010 Mar 5;12(5):1140-3. doi: 10.1021/ol1001818.

Abstract

A hydrogen bonding-mediated double Michael addition-aromatization cascade of 2-propenylindoles and nitroolefins has been disclosed. The methodology allows an efficient synthesis of diverse and structurally complex tetrahydrocarbazoles in good to excellent enantioselectivities and diastereoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Carbazoles / chemistry*
  • Catalysis
  • Hydrogen Bonding
  • Stereoisomerism
  • Substrate Specificity
  • Sulfonamides / chemistry

Substances

  • Alkenes
  • Carbazoles
  • Sulfonamides
  • 1,2,3,4-tetrahydrocarbazole