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  • Rhodium(I)-Catalysed Annulation of Bicyclo[1.1.0]butyl-Substituted Dihydroquinolines and Dihydropyridines

    • Rhodium(I)-Catalysed Annulation of Bicyclo[1.1.0]butyl-Substituted Dihydroquinolines and Dihydropyridines

    Title Rhodium(I)-Catalysed Annulation of Bicyclo[1.1.0]butyl-Substituted Dihydroquinolines and Dihydropyridines
    Authors Matteo Borgini, Qi-Nan Huang, Pan-Pan Chen, Steven J. Geib, K. N. Houk, Peter Wipf
    Magazine Journal of the American Chemical Society
    Date 05/20/2024
    DOI https://doi.org/10.1021/jacs.4c04081
    Introduction Compounds containing bicyclo[1.1.0]butane exhibit unique chemical reactivity, initiating 'strain-release' reaction cascades and providing novel scaffolds with significant utility in drug development. This study presents the synthesis of new bicyclo[1.1.0]butane-linked heterocycles via nucleophilic addition of bicyclo[1.1.0]butyl anions to 8-isocyanatoquinoline or iminium cations derived from quinolines and pyridines. The resulting bicyclo[1.1.0]butanes are highly regioselectively converted into unprecedented bridged heterocycles through a rhodium(I)-catalysed annulative rearrangement. This addition/rearrangement process accommodates a wide range of functional groups. Subsequent chemo- and stereoselective synthetic transformations of urea, alkene, cyclopropane, and aniline moieties of the 1-methylene-5-azacyclopropa[cd]indene scaffolds yield several additional new heterocyclic building blocks. X-ray structure-validated quantum mechanical DFT calculations of the reaction pathway indicate the intermediacy of rhodium carbenoid and metallocyclobutane species.
    Quote Matteo Borgini, Qi-Nan Huang and Pan-Pan Chen et al. Rhodium(I)-Catalysed Annulation of Bicyclo[1.1.0]butyl-Substituted Dihydroquinolines and Dihydropyridines. J. Am. Chem. Soc. 2024. DOI: 10.1021/jacs.4c04081
    Element Rhodium (Rh)
    Materials Chemical Compounds
    Industry Chemical & Pharmacy
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