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Keywords:

  • Nitrogen heterocycles;
  • Asymmetric catalysis;
  • Nucleophilic addition;
  • Bifunctional catalysis

Abstract

Nearly a century after the first report of the Reissert reaction the first catalytic, asymmetric example was published. Since then there have been a small number of reports of similar reaction types: activation of nitrogen-containing aromatic rings through alkylation or acylation, followed by the addition of a carbon-centered nucleophile to the ring. These reactions place great demands on catalyst design; many of the catalysts are bifunctional, simultaneously activating both nucleophiles and electrophiles. The structures obtained from such reactions may easily be derivatized into natural products or drug-like structures. Despite the elegance of the known examples, there are still many reaction types that have not been reported.