Tandem Functionalization of
Nonactivated Alkenes and Alkynes in
Intramolecular <i>N</i>-Acyloxyiminium Ion
Carbocyclization. Synthesis of
6-Substituted Hydroindole 2-Carboxylic
Acids
Stephen Hanessian
Martin Tremblay
10.1021/ol040053b.s002
https://acs.figshare.com/articles/journal_contribution/Tandem_Functionalization_of_Nonactivated_Alkenes_and_Alkynes_in_Intramolecular_i_N_i_Acyloxyiminium_Ion_Carbocyclization_Synthesis_of_6_Substituted_Hydroindole_2_Carboxylic_Acids/3312910
Five-membered <i>N</i>-Boc acyliminium ions derived from l-pyroglutamic acid harboring 4-butenyl and 4-butynyl tethers undergo Lewis acid-mediated halo and tandem Friedel−Crafts carbocyclization within minutes at −78 °C to give stereodefined 6-substituted octahydroindole and
hexahydroindole 2-carboxylic acid methyl esters, respectively. The cyclic vinyl bromides are excellent substrates for Pd-catalyzed Suzuki−Miyaura, Heck, and Stille couplings. The method also provides access to enantiopure sp<sup>2</sup>- and sp<sup>3</sup>-arylated azabicyclics that are novel and
versatile scaffolds for chemical diversification.
2004-12-09 00:00:00
esters
tandem Functionalization
octahydroindole
butenyl
Intramolecular N
halo
Synthesi
methyl
carboxylic
Alkyne
Heck
arylated azabicyclics
substrate
sp 3
carbocyclization
cyclic vinyl bromides
acid
Suzuki
tethers
chemical diversification
scaffold
access
Substituted
method
stereodefined
enantiopure sp 2
Hydroindole
hexahydroindole
butynyl
Carboxylic
Nonactivated Alkenes
Acyloxyiminium Ion Carbocyclization
Friedel
Acid
Lewis
Boc acyliminium ions
Stille couplings