Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates

Caroline Joannesse, Louis C. Morrill, Craig D. Campbell, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the alpha-regioisomers (alpha/gamma up to 83:17) with high asymmetric induction (up to 83% ee).

Original languageEnglish
Pages (from-to)1865-1879
Number of pages15
JournalSynthesis
Issue number12
DOIs
Publication statusPublished - Jun 2011

Keywords

  • isothiourea
  • organocatalysis
  • carboxyl transfer
  • furanyl carbonates
  • butenolides
  • ACYL-TRANSFER CATALYST
  • SECONDARY BENZYLIC ALCOHOLS
  • STEGLICH REARRANGEMENT REACTION
  • EFFECTIVE KINETIC RESOLUTION
  • ENANTIOSELECTIVE SYNTHESIS
  • TETRAMISOLE DERIVATIVES
  • NUCLEOPHILIC CATALYSTS
  • BENZOIC ANHYDRIDES
  • PIVALIC ANHYDRIDE
  • QUATERNARY CARBON

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