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Carbene-Catalyzed Reaction of Indolyl Methylenemalononitriles and Enals for Access to Complex Tetrahydrocarbazoles.

Chengli MouLiejin ZhouRunjiang SongHuifang ChaiLin HaoYonggui Robin Chi
Published in: Organic letters (2020)
A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers.
Keyphrases
  • room temperature
  • electron transfer
  • ionic liquid
  • mass spectrometry
  • molecular dynamics simulations
  • energy transfer