%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