Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol

Adele Faulkner, James S. Scott, John F. Bower*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

44 Citations (Scopus)

Abstract

We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to alpha,alpha-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.

Original languageEnglish
Pages (from-to)1521-1523
Number of pages3
JournalChemical Communications
Volume49
Issue number15
DOIs
Publication statusPublished - 2013

Keywords

  • KETONE O-PENTAFLUOROBENZOYLOXIMES
  • HECK REACTIONS
  • ENANTIOSELECTIVE SYNTHESIS
  • AMMONIUM-SALTS
  • DERIVATIVES
  • REARRANGEMENT
  • INSERTION
  • ALKYNES
  • PHOSPHORAMIDITES
  • STEREOCENTERS

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