Phosphonamide Stabilized Allylic Carbanions. New Homoenolate Anion Equivalents

David A. Evans, James M. Takacs, Kenneth M. Hurst

Research output: Contribution to journalArticlepeer-review

113 Scopus citations


The chemistry of phosphonamide stabilized allylic carbanions derived from the 1,2-addition of tervalent phosphorus siloxanes with α,β-unsaturated aldehydes has been studied. An in situ synthesis of allylic α-silyloxyphosphonamides, followed by metalation and regioselective γ-alkylation of the allylic carbanion, yields a versatile “active ester”. Transesterification under mild conditions gives esters and lactones and defines a new homoenolate equivalency.

Original languageEnglish (US)
Pages (from-to)371-378
Number of pages8
JournalJournal of the American Chemical Society
Issue number2
StatePublished - Feb 1 1979
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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