Synthesis of enantioenriched α,α-disubstituted cyclopentenes catalyzed by N-heterocyclic carbenes

Eric M. Phillips, Manabu Wadamoto, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The desymmetrization of 1,3-diketones using N-heterocyclic carbenes results in the formation of highly enantioenriched cyclopentenes in good yield. The reaction proceeds through a catalytic intramolecular aldol reaction and subsequent β-lactone formation. The expulsion of carbon dioxide at mild reaction temperatures affords the cyclopentene products.

Original languageEnglish (US)
Pages (from-to)687-690
Number of pages4
JournalSynthesis
Issue number4
DOIs
StatePublished - 2009

Keywords

  • Aldol reactions
  • Asymmetric catalysis
  • Carbenes
  • Umpolung
  • β-lactones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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