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Communication | Special issue | Vol 67, No. 2, 2006, pp.511-518
Published online, 6th December, 2005
DOI: 10.3987/COM-05-S(T)47
Solid-phase Pyrrolidine Synthesis via 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated by the Decarboxylative Route

Batia Ben-Aroya Bar-Nir and Moshe Portnoy*

*School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv, 69978, Israel

Abstract

Although solid-phase pyrrolidine synthesis via dipolar cycloaddition of ester-stabilized azomethine ylides has been demonstrated on several occasions, this reaction with nonstabilized azomethine ylides, generated on solid support by a decarboxylative pathway, has never been reported. Herein we present the first solid-phase synthesis of pyrrolidines via this route and demonstrate that the reacting azomethine ylide can be generated both from a resin-bound aldehyde or amino acid. Using cyclic and acyclic dipolarophiles, bi- and monocyclic resin-bound pyrrolidines were obtained. The modest to high degree of regio- and diastereoselectivity observed in the reaction can be tuned by the substituents of the partners of this three-component process.