Atroposelective Synthesis of Tetrahydropyrrolo[3,2‐c]azepine Derivatives Through Gold(I)‐Catalyzed Hydroarylation

A series of enantioenriched substituted tetrahydropyrrolo[3,2‐c]azepine products possessing an axial chirality were synthesized in 63–99% yield through a gold(I)‐catalyzed hydroarylation. DFT calculations rationalized the reactivity observed for the formation of such complex molecular frameworks and...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-12, Vol.364 (24), p.4415-4420
Main Authors: Gaignard‐Gaillard, Quentin, Han, Xu, Alix, Aurélien, Bour, Christophe, Guillot, Regis, Gandon, Vincent, Voituriez, Arnaud
Format: Article
Language:English
Subjects:
Axial chirality
Chemical Sciences
Gold catalysis
Hydroarylation
Pyrrolo[3,2-c]azepines
Stereoselectivity
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Summary:A series of enantioenriched substituted tetrahydropyrrolo[3,2‐c]azepine products possessing an axial chirality were synthesized in 63–99% yield through a gold(I)‐catalyzed hydroarylation. DFT calculations rationalized the reactivity observed for the formation of such complex molecular frameworks and guided our choice in the pyrrole N‐substituent to isolate configurationally stable compounds.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200828