Solid-phase synthesis: Intramolecular azomethine ylide cycloaddition (→ proline) and carbanilide cyclization (→ hydantoin) reactions

YD Gong, S Najdi, MM Olmstead…

Index: Gong, Young-Dae; Najdi, Samir; Olmstead, Marilyn M.; Kurth, Mark J. Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 3081 - 3086

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Citation Number: 71

Abstract

An efficient, diastereoselective route to 2, 5, 6, 7-tetrasubstituted-1 H-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 ...