%0 Journal Article
%A Gong, Young-Dae
%A Najdi, Samir
%A Olmstead, Marilyn M.
%A Kurth, Mark J.
%D 1998
%T Solid-Phase Synthesis: Intramolecular Azomethine Ylide
Cycloaddition (→Proline) and Carbanilide Cyclization
(→Hydantoin) Reactions
%U https://acs.figshare.com/articles/journal_contribution/Solid-Phase_Synthesis_Intramolecular_Azomethine_Ylide_Cycloaddition_Proline_and_Carbanilide_Cyclization_Hydantoin_Reactions/3709503
%R 10.1021/jo9800210.s001
%2 https://acs.figshare.com/ndownloader/files/5800059
%K carbanilide cyclization chemistries
%K Cyclization
%K Experiment
%K intramolecular
%K pyrrolo
%K Proline
%K cycloaddition
%K diastereoselective route
%K Ylide
%K Hydantoin
%K tetrasubstituted
%K glycinate
%K Azomethine
%K Synthesi
%K spacer moiety
%K ylide
%K dipolar
%K stereoselectivity
%K cyclative release step
%K phase
%K azomethine
%K resin
%K Cycloaddition
%K Intramolecular
%K Carbanilide
%K imidazole
%X An efficient, diastereoselective route to
2,5,6,7-tetrasubstituted-1H-pyrrolo[1,2-c]imidazoles
has been
developed using solid-phase intramolecular azomethine ylide
cycloaddition and carbanilide cyclization chemistries. To successfully execute this eight-step protocol
in the solid phase, it was necessary
to insert a spacer moiety between the resin and glycinate functional
group. Experiments addressing
the stereoselectivity of the 1,3-dipolar cycloaddition step as well as
the cyclative release step are
also presented.
%I ACS Publications