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

Lookup NU author(s): Dr Julian Knight, Dr Paul Stoker, Dr Kirill Tchabanenko, Dr Simon Harwood

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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. © 2008 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Knight JG, Stoker PA, Tchabanenko K, Harwood SJ, Lawrie KWM

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2008

Volume: 64

Issue: 17

Pages: 3744-3750

Print publication date: 21/04/2008

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Elsevier Ltd

URL: http://dx.doi.org/10.1016/j.tet.2008.02.019

DOI: 10.1016/j.tet.2008.02.019

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