Org Lett. 2010 Apr 2;12(7):1396-9.

Highly diastereoselective synthesis of substituted pyrrolidines using a sequence of azomethine ylide cycloaddition and nucleophilic cyclization.

Bélanger G, Darsigny V, Doré M, Lévesque F.

Source

Département 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.

PMID:: 20192221; [PubMed - indexed for MEDLINE]

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