Vinzenz Thönnnißen, Johannes Westphäling, Iuliana L. Atodiresei, Frederic W. Patureau

Atroposelective Chan‐Evans‐Lam Amination

  • General Chemistry
  • Catalysis
  • Organic Chemistry

The synthetic control of atropoisomerism along C─N bonds is a major challenge, and methods that allow C─N atroposelective bond formation are rare. This is a problem because each atropoisomer can feature starkly differentiated biological properties. Yet, among the three most practical and applicable classical amination methods available: 1) the Cu‐catalyzed Ullmann‐Goldberg reaction, 2) the Pd‐catalyzed Buchwald‐Hartwig reaction, and 3) the Cu‐catalyzed Chan‐Evans‐Lam reaction, none has truly been rendered atroposelective at the newly formed C─N bond. The first ever Chan‐Evans‐Lam atroposelective amination is herein described with a simple copper catalyst and newly designed PyrOx chiral ligand. This method should find important applications in asymmetric synthesis, in particular for medicinal chemistry.

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