%0 Journal Article
%A Hanessian, Stephen
%A Tremblay, Martin
%D 2004
%T Tandem Functionalization of
Nonactivated Alkenes and Alkynes in
Intramolecular N-Acyloxyiminium Ion
Carbocyclization. Synthesis of
6-Substituted Hydroindole 2-Carboxylic
Acids
%U 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
%R 10.1021/ol040053b.s002
%2 https://acs.figshare.com/ndownloader/files/5151640
%K esters
%K tandem Functionalization
%K octahydroindole
%K butenyl
%K Intramolecular N
%K halo
%K Synthesi
%K methyl
%K carboxylic
%K Alkyne
%K Heck
%K arylated azabicyclics
%K substrate
%K sp 3
%K carbocyclization
%K cyclic vinyl bromides
%K acid
%K Suzuki
%K tethers
%K chemical diversification
%K scaffold
%K access
%K Substituted
%K method
%K stereodefined
%K enantiopure sp 2
%K Hydroindole
%K hexahydroindole
%K butynyl
%K Carboxylic
%K Nonactivated Alkenes
%K Acyloxyiminium Ion Carbocyclization
%K Friedel
%K Acid
%K Lewis
%K Boc acyliminium ions
%K Stille couplings
%X Five-membered N-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 sp2- and sp3-arylated azabicyclics that are novel and
versatile scaffolds for chemical diversification.
%I ACS Publications