10.1021/jo9800210.s001
Young-Dae Gong
Young-Dae
Gong
Samir Najdi
Samir
Najdi
Marilyn M. Olmstead
Marilyn M.
Olmstead
Mark J. Kurth
Mark J.
Kurth
Solid-Phase Synthesis: Intramolecular Azomethine Ylide
Cycloaddition (→Proline) and Carbanilide Cyclization
(→Hydantoin) Reactions
American Chemical Society
1998
carbanilide cyclization chemistries
Cyclization
Experiment
intramolecular
pyrrolo
Proline
cycloaddition
diastereoselective route
Ylide
Hydantoin
tetrasubstituted
glycinate
Azomethine
Synthesi
spacer moiety
ylide
dipolar
stereoselectivity
cyclative release step
phase
azomethine
resin
Cycloaddition
Intramolecular
Carbanilide
imidazole
1998-04-09 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Solid-Phase_Synthesis_Intramolecular_Azomethine_Ylide_Cycloaddition_Proline_and_Carbanilide_Cyclization_Hydantoin_Reactions/3709503
An efficient, diastereoselective route to
2,5,6,7-tetrasubstituted-1<i>H</i>-pyrrolo[1,2-<i>c</i>]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.