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Keywords:

  • cinchona alkaloids;
  • Grignard reaction;
  • heterocycles;
  • neighboring-group effects;
  • nucleophilic addition
Thumbnail image of graphical abstract

Aminal pharm: Grignard reagents undergo a surprising nucleophilic aromatic addition reaction to cinchona alkaloids to stereoselectively produce cyclic aminals. Structurally diverse alkaloid derivatives with rigid cores that bear reactive functional groups (see examples) can be readily synthesized by this simple nucleophilic alkylation protocol.