Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

Julian G. Knight, Paul A. Stoker, Kirill Tchabanenko, Simon J. Harwood, Kenneth W. M. Lawrie

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide.
Original languageEnglish
Pages (from-to)3744-3750
Number of pages7
JournalTetrahedron
Volume64
Issue number17
DOIs
Publication statusPublished - 21 Apr 2008

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