Stereoselective Synthesis of Functionalized Pyrrolidines by Ruthenium Porphyrin-Catalyzed Decomposition of α-Diazo Esters and Cascade Azomethine Ylide Formation/1,3-Dipolar Cycloaddition Reactions

Abstract

[reaction: see text] Ruthenium porphyrins catalyze three-component coupling reaction of alpha-diazo esters with a series of N-benzylidene imines and alkenes to form functionalized pyrrolidines in excellent diastereoselectivities. The reaction proceeds via a reactive ruthenium-carbene intermediate and its subsequent reaction with imine to generate azomethine ylide, which reacts with alkenes via 1,3-diploar cycloaddition.