Organic base effects in NHC promoted O- to C-carboxyl transfer; chemoselectivity profiles, mechanistic studies and domino catalysis

Craig D. Campbell, Christopher J. Collett, Jennifer E. Thomson, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

The O- to C-carboxyl transfer of oxazolyl carbonates promoted by triazolinylidenes, generated in situ with NEt3, shows a markedly different rate and chemoselectivity profile to the same reaction promoted by triazolinylidenes generated using KHMDS. The mechanism of these pathways has been probed through extensive crossover studies to understand this process. The use of NEt3 as a base allows domino multi-step reaction sequences to be developed, although chiral NHCs only generate modest levels of asymmetric induction (<15% ee) in these domino reaction processes.

Original languageEnglish
Pages (from-to)4205-4218
Number of pages14
JournalOrganic & Biomolecular Chemistry
Volume9
Issue number11
DOIs
Publication statusPublished - 2011

Keywords

  • N-HETEROCYCLIC CARBENE
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • INTERMOLECULAR STETTER REACTION
  • STEGLICH REARRANGEMENT REACTION
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • NUCLEOPHILIC CATALYSTS
  • ASYMMETRIC-SYNTHESIS
  • GAMMA-BUTYROLACTONES
  • KINETIC RESOLUTION
  • STABLE CARBENES

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