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.
ASJC Scopus subject areas
- Organic Chemistry