Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral

James Douglas, Gwydion Churchill, Alexandra Martha Zoya Slawin, David J. Fox, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)
1 Downloads (Pure)

Abstract

Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94 % ee) or α-chloroesters (up to 94 % ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.
Original languageEnglish
Pages (from-to)16354–16358
JournalChemistry - A European Journal
Volume21
Issue number46
Early online date25 Sept 2015
DOIs
Publication statusPublished - 9 Nov 2015

Keywords

  • Asymmetric catalysis
  • Chlorination reactions
  • Ketenes
  • Lactones
  • Stereodivergent reactions

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