10.1021/acs.orglett.6b01376.s001
Jacob
R. Stepherson
Jacob
R.
Stepherson
Caitlan E. Ayala
Caitlan E.
Ayala
Thomas H. Tugwell
Thomas H.
Tugwell
Jeffrey L. Henry
Jeffrey L.
Henry
Frank
R. Fronczek
Frank
R.
Fronczek
Rendy Kartika
Rendy
Kartika
Carbazole Annulation via Cascade Nucleophilic Addition–Cyclization
Involving 2‑(Silyloxy)pentadienyl Cation
American Chemical Society
2016
cation
ether
functionalized carbazoles
indole
intramolecular dehydrative cyclization
Carbazole Annulation
Silyloxy
cascade reactions
strategy
intermediate
sequence
synthesis
Nucleophilic
silyloxy
Br ønsted acid catalysis
silyl
regioselective nucleophilic addition
ionization
Cascade
hydroxy
enol
yield
Cation
electrophilic species
scaffold
2016-06-03 23:45:14
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Carbazole_Annulation_via_Cascade_Nucleophilic_Addition_Cyclization_Involving_2_Silyloxy_pentadienyl_Cation/3413314
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.