A Novel Approach to Substituted α-Carbamoyl Phosphonates: Useful Reagents for the Horner-Wadsworth-Emmons Olefination

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2 Scopus citations

Abstract

α-Carbamoyl phosphonates are useful reagents for the Horner-Wadsworth-Emmons olefination of aldehydes en route to medicinally relevant polysubstituted acrylamides. A new synthetic approach to these reagents has been developed. The methodology relies on the microwave-promoted Wolff rearrangement of α-acyl-α-diazophosphonates with trapping of the ketene intermediate in situ with various amines.

Original languageEnglish
JournalSynlett
DOIs
StateE-pub ahead of print - 20 Jun 2020

Scopus subject areas

  • Organic Chemistry

Keywords

  • Horner-Wadsworth-Emmons olefination
  • ketene trapping
  • Michael acceptors
  • one-pot procedure
  • Wolff rearrangement
  • α-diazo-β-oxophosphonates

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