Chiral nitrogen-containing five-membered rings, particularly highly functionalized chiral pyrrolidine skeletons, are core structural units in many drugs and biologically active molecules. Their asymmetric catalytic synthesis has long been a research hotspot in the field of organic synthesis. Among the various approaches, the asymmetric 1,3-dipolar cycloaddition reaction between azomethine ylides and activated olefins is one of the most direct and efficient methods for constructing such compounds.
Currently, research on the construction of pyrrolidines through the reaction of azomethine ylides and olefins mainly focuses on metal-catalyzed two-component reactions, while reports on organocatalysis and multi-component strategies are relatively limited. In our work, we designed bifunctional quaternary phosphonium salts as catalysts to promote the asymmetric three-component 1,3-dipolar cycloaddition reaction involving exocyclic olefins, aldehydes, and amino esters, thereby constructing highly functionalized spiro-pyrrolidine derivatives and offering a new strategy for the stereoselective synthesis of such nitrogen-containing heterocycles.
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