Solid-phase pyrrolidine synthesis via 1,3-dipolar cycloaddition of azomethine ylides generated by the decarboxylative route

Batia Ben Aroya Bar-Nir*, Moshe Portnoy

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish
Pages (from-to)511-518
Number of pages8
JournalHeterocycles
Volume67
Issue number2
DOIs
StatePublished - 1 Feb 2006

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