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 guided our choice in the pyrrole N-substituent to isolate configurationally stable compounds.

Automated summary

A series of enantioenriched substituted tetrahydropyrrolo[3,2-c]azepine products with axial chirality were synthesized in 63-99% yield through a gold(I)-catalyzed hydroarylation. DFT calculations rationalized the observed reactivity and guided the choice of pyrrole N-substituent to isolate configurationally stable compounds.