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

Academic Article

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.
  • Authors

    Published In

  • Tetrahedron  Journal
  • Digital Object Identifier (doi)

    Author List

  • Knight JG; Stoker PA; Tchabanenko K; Harwood SJ; Lawrie KWM
  • Start Page

  • 3744
  • End Page

  • 3750
  • Volume

  • 64
  • Issue

  • 17