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Solid-Phase Synthesis: Intramolecular Azomethine Ylide Cycloaddition (→Proline) and Carbanilide Cyclization (→Hydantoin) Reactions
journal contribution
posted on 1998-04-09, 00:00 authored by Young-Dae Gong, Samir Najdi, Marilyn M. Olmstead, Mark J. KurthAn 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.
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carbanilide cyclization chemistriesCyclizationExperimentintramolecularpyrroloProlinecycloadditiondiastereoselective routeYlideHydantointetrasubstitutedglycinateAzomethineSynthesispacer moietyylidedipolarstereoselectivitycyclative release stepphaseazomethineresinCycloadditionIntramolecularCarbanilideimidazole
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