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Solid-Phase Synthesis:  Intramolecular Azomethine Ylide Cycloaddition (→Proline) and Carbanilide Cyclization (→Hydantoin) Reactions

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posted on 1998-04-09, 00:00 authored by Young-Dae Gong, Samir Najdi, Marilyn M. Olmstead, Mark J. Kurth
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.

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