Generation and Application of Homoenolate Equivalents Utilizing [1,2]-Phospha-Brook Rearrangement under Brønsted Base Catalysis

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20 Citations (Scopus)

Abstract

A new method for catalytic generation of a homoenolate equivalent and its application to carbon−carbon bond formation was developed by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The α-oxygenated allyl anions, which can serve as homoenolate equivalents, were catalytically generated in situ by treating readily available chalcones with diethyl phosphite or the pre-formed 1,2-adducts of diethyl phosphite with chalcones in the presence of a catalytic amount of a phosphazene base, P2-tBu. The resulting allyl anions were subsequently trapped by various electrophiles, including Michael acceptors, imines, and aldehydes, providing the corresponding adducts in good yields with moderate to good diastereoselectivities.

Original languageEnglish
Pages (from-to)2769-2773
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number12
DOIs
Publication statusPublished - 2017 Feb 24

Keywords

  • Brønsted base catalysis
  • [1,2]-phospha-brook rearrangement
  • homoenolate
  • organocatalyst
  • umpolung

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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