Carbazole Annulation via Cascade Nucleophilic Addition-Cyclization Involving 2-(Silyloxy)pentadienyl Cation
| Autor: | Rendy Kartika, Jeffrey L. Henry, Frank R. Fronczek, Jacob R. Stepherson, Thomas H. Tugwell, Caitlan E. Ayala |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Annulation
Nucleophilic addition Silylation 010405 organic chemistry Carbazole Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Enol Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Electrophile Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 18(12) |
| ISSN: | 1523-7052 |
| Popis: | 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 Bronsted 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|