N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

Carmen Concellon, Nicolas Duguet, Andrew D. Smith

Research output: Contribution to journalReview articlepeer-review

67 Citations (Scopus)

Abstract

Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

Original languageEnglish
Pages (from-to)3001-3009
Number of pages9
JournalAdvanced Synthesis & Catalysis
Volume351
Issue number17
DOIs
Publication statusPublished - Nov 2009

Keywords

  • asymmetric catalysis
  • enantioselectivity
  • esters
  • ketenes
  • N-heterocyclic carbenes
  • organocatalysis
  • INTERMOLECULAR STETTER REACTION
  • DIELS-ALDER REACTIONS
  • METHYL ALPHA-PHENYLPROPIONATE
  • RING-OPENING POLYMERIZATION
  • SYNTHESEN MIT KETENEN
  • LOW CATALYST LOADINGS
  • C-CARBOXYL TRANSFER
  • ASYMMETRIC-SYNTHESIS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • LIVING POLYMERIZATION

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