Pd-catalyzed enantioselective access to hydrocarbazolones containing contiguous quaternary and tertiary stereocenters.

ABSTRACT: The hydrocarbazole scaffold represents the core structure of numerous monoterpenoid indole alkaloids. The development of catalytic methods that provide efficient access to enantioenriched hydrocarbazole derivatives is central for the synthesis of these bioactive alkaloids. We report here a palladium-catalyzed enantioselective formal 5-endo arylative cyclization of enaminones, facilitating the construction of hexahydrocarbazol-4-ones containing contiguous C4a-quaternary and C9a-tertiary stereocenters with high enantioselectivities (86.5 : 13.5-99 : 1 er) and diastereoselectivities (>20 : 1 dr). Notably, enaminone substrates bearing an α-allyl group undertake an arylation/Cope rearrangement cascade, offering a unique route to C1-substituted tetrahydrocarbazol-4-ones. A stereodivergent

SUBMITTER: Sun H 

PROVIDER: S-EPMC11912222 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature