NHC-Mediated Chlorination of Unsymmetrical Ketenes: Catalysis and Asymmetry

James Douglas, Kenneth B. Ling, Carmen Concellon, Gwydion Churchill, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

NHCs promote the efficient chlorination of unsymmetrical disubstituted ketenes with a range of chlorinating agents; chiral NHCs display promising levels of asymmetric induction in the chlorination process with up to 61 % ee observed using 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone.

Original languageEnglish
Pages (from-to)5863-5869
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - Oct 2010

Keywords

  • Homogeneous catalysis
  • Asymmetric synthesis
  • N-Heterocyclic carbene
  • Ketenes
  • Chlorination
  • N-HETEROCYCLIC CARBENE
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • C-CARBOXYL TRANSFER
  • BETA-KETO-ESTERS
  • ALPHA-CHLORINATION
  • KINETIC RESOLUTION
  • CARBONYL-COMPOUNDS
  • ACID-CHLORIDES
  • QUATERNARY STEREOCENTERS
  • 1,3-DICARBONYL COMPOUNDS

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