Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer

J E Thomson, K Rix, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

94 Citations (Scopus)

Abstract

An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.

Original languageEnglish
Pages (from-to)3785-3788
Number of pages4
JournalOrganic Letters
Volume8
Issue number17
DOIs
Publication statusPublished - 17 Aug 2006

Keywords

  • INTRAMOLECULAR STETTER REACTION
  • NUCLEOPHILIC CARBENES
  • TRANSESTERIFICATION/ACYLATION REACTIONS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • LIVING POLYMERIZATION
  • GAMMA-BUTYROLACTONES
  • QUATERNARY CARBON
  • 1ST EXAMPLE
  • ACYLATION
  • ESTERS

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