Carbazole Annulation via Cascade Nucleophilic Addition-Cyclization Involving 2-(Silyloxy)pentadienyl Cation
© 2016 American Chemical Society. We report a new strategy toward the synthesis of highly functionalized carbazoles via 2-(silyloxy)pentadienyl cation intermediates, which were generated upon ionization of vinyl-substituted α-hydroxy silyl enol ethers under Brønsted acid catalysis. These electrophilic species were found to readily undergo cascade reactions with substituted indoles to generate carbazole molecular scaffolds in good yields via a sequence of regioselective nucleophilic addition, followed by intramolecular dehydrative cyclization.
Publication Source (Journal or Book title)
Stepherson, J., Ayala, C., Tugwell, T., Henry, J., Fronczek, F., & Kartika, R. (2016). Carbazole Annulation via Cascade Nucleophilic Addition-Cyclization Involving 2-(Silyloxy)pentadienyl Cation. Organic Letters, 18 (12), 3002-3005. https://doi.org/10.1021/acs.orglett.6b01376