Login / Signup

Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction.

Jamie R AllenAna BahamondeYukino FurukawaMatthew S Sigman
Published in: Journal of the American Chemical Society (2019)
The development of an intermolecular and enantioselective aza-Wacker reaction is described. Using indoles as the N-source and a selection of alkenols as the coupling partners selective β-hydride elimination toward the alcohol was achieved. This strategy preserves the newly formed stereocenter by preventing the formation of traditionally observed enamine products. Allylic and homoallylic alcohols with a variety of functional groups are compatible with the reaction in high enantioselectivity. Isotopic-labeling experiments support a syn amino-palladation mechanism for this new class of aza-Wacker reactions.
Keyphrases
  • electron transfer
  • room temperature
  • hepatitis c virus
  • alcohol consumption
  • hiv testing
  • human immunodeficiency virus
  • men who have sex with men