Intramolecular Azomethine Ylide Research Articles

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

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.

ChemInform Abstract: Consecutive Intramolecular Azomethine Ylide Cycloaddition‐Pummerer Rearrangement as a Strategy for the Synthesis of Enantiomerically Pure 5‐(Hydroxymethyl)prolines.

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Intermolecular and intramolecular azomethine ylide [3 + 2] dipolar cycloadditions for the synthesis of highly functionalized pyrroles and pyrrolidines

Intermolecular and intramolecular azomethine ylide [3 + 2] dipolar cycloadditions for the synthesis of highly functionalized pyrroles and pyrrolidines