ol6b01376_si_001.pdf (4.62 MB)
Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization Involving 2‑(Silyloxy)pentadienyl Cation
journal contribution
posted on 2016-06-03, 23:45 authored by Jacob
R. Stepherson, Caitlan E. Ayala, Thomas H. Tugwell, Jeffrey L. Henry, Frank
R. Fronczek, Rendy KartikaWe 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.
History
Usage metrics
Categories
Keywords
cationetherfunctionalized carbazolesindoleintramolecular dehydrative cyclizationCarbazole AnnulationSilyloxycascade reactionsstrategyintermediatesequencesynthesisNucleophilicsilyloxyBr ønsted acid catalysissilylregioselective nucleophilic additionionizationCascadehydroxyenolyieldCationelectrophilic speciesscaffold
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC