Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: Asymmetric synthesis of highly substituted β-lactones

Daniel T. Cohen*, Chad C. Eichman, Eric M. Phillips, Emily R. Zarefsky, Karl A. Scheidt

*Corresponding author for this work

Research output: Contribution to journalArticle

76 Scopus citations

Abstract

New DKR type: An N-heterocyclic carbene (NHC)-catalyzed dynamic kinetic resolution of racemic α-substituted β-keto esters has been developed. This method relies on the epimerization of an NHC-enol intermediate before subsequent aldol/acylation events. Highly substituted β-lactones are produced in good yield with good to excellent selectivities (see scheme).

Original languageEnglish (US)
Pages (from-to)7309-7313
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number29
DOIs
StatePublished - Jul 16 2012

Keywords

  • Aldols
  • Asymmetric synthesis
  • Dynamic kinetic resolution
  • Homoenolates
  • N-heterocyclic carbenes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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