Probing the efficiency of N-heterocyclic carbene promoted O- to C-carboxyl transfer of oxazolyl carbonates

Jennifer E. Thomson, Craig D. Campbell, Carmen Concellon, Nicolas Duguet, Kathryn Rix, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

Original languageEnglish
Pages (from-to)2784-2791
Number of pages8
JournalThe Journal of Organic Chemistry
Volume73
DOIs
Publication statusPublished - 4 Apr 2008

Keywords

  • INTRAMOLECULAR STETTER REACTION
  • ALPHA-AMINO-ACIDS
  • KINETIC RESOLUTION
  • ENANTIOSELECTIVE ACYLATION
  • NUCLEOPHILIC CARBENES
  • TRANSESTERIFICATION/ACYLATION REACTIONS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • STEREOSELECTIVE-SYNTHESIS
  • MULTICOMPONENT REACTIONS
  • LIVING POLYMERIZATION

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