Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

Pei-Pei Yeh, David S. B. Daniels, David B. Cordes, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

92 Citations (Scopus)

Abstract

A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

Original languageEnglish
Pages (from-to)964-967
Number of pages4
JournalOrganic Letters
Volume16
Issue number3
Early online date16 Jan 2014
DOIs
Publication statusPublished - 7 Feb 2014

Keywords

  • Bicyclic-Beta-Lactones
  • Catalyzed Aldol-Lactonization
  • Acyl Transfer Catalyst
  • Asymmetric-Synthesis
  • Dyotropic Rearrangements
  • Ncal Reactions
  • Keto Acids
  • 3,5-dibromo-2-pyrone

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