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Updated: Jun 15, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Highly diastereoselective synthesis of substituted pyrrolidines using a sequence of azomethine ylide cycloaddition
Guillaume Bélanger1, Véronique Darsigny, Michaël Doré
1Département de Chimie, Université de Sherbrooke, 2500 Boulevard Université, Sherbrooke, Québec J1K 2R1, Canada. guillaume.belanger@usherbrooke.ca
Abstract:
Although cycloadditions of azomethine ylides usually give mixtures of endo/exo adducts, we successfully tuned the mechanistic path of a new reaction cascade to afford substituted pyrrolidines in high yields and diastereomeric purity. This was achieved by forcing the demetalation of tin- or silicon-substituted iminium ions, followed by azomethine ylide cycloaddition and nucleophilic cyclization. Structural complexity is thus built rapidly in a fully controlled one-pot reaction cascade.
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