Brønsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones

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Abstract

A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Brønsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.

Original languageEnglish
Pages (from-to)585-588
Number of pages4
JournalChemistry - A European Journal
Volume27
Issue number2
DOIs
Publication statusPublished - 2021 Jan 7

Keywords

  • Brønsted base catalysis
  • annulation
  • lactams
  • reduction
  • tandem catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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