Title
Carbazole Annulation via Cascade Nucleophilic Addition-Cyclization Involving 2-(Silyloxy)pentadienyl Cation
Document Type
Article
Publication Date
6-17-2016
Abstract
© 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)
Organic Letters
First Page
3002
Last Page
3005
Recommended Citation
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