Atroposelective Chan–Evans–Lam Amination

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...

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Bibliographic Details
Published in:	Chemistry : a European journal 2024-03, Vol.30 (16), p.e202304378-n/a
Main Authors:	Thönnißen, Vinzenz, Westphäling, Johannes, Atodiresei, Iuliana L., Patureau, Frederic W.
Format:	Article
Language:	eng
Subjects:	Amination Asymmetric synthesis atroposelective amination Biological properties Catalysts Chan–Evans–Lam reaction Chemical synthesis Copper enantioselective catalysis PyrOx ligand VPOX
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Summary:	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. The first and long elusive atroposelective Chan–Evans–Lam C−N coupling is herein described. This strategy should find important applications for the enantioselective synthesis of bioactive compounds containing hindered carbon‐nitrogen bonds.
ISSN:	0947-6539 1521-3765