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[2 + 4] Annulation of Alkyl(phenyl)phosphinic Chlorides with Enones: Stereoselective Synthesis of δ-Phosphinolactones.

Xin YuanXuan KeJiaxi Xu
Published in: Organic letters (2022)
Various δ-phosphinolactones (δ-phostines) are efficiently and diastereospecifically synthesized in good to excellent yields from direct [2 + 4] annulation of alkyl(phenyl)phosphinic chlorides and α,β-enones in the presence of LiHMDS. The annulation involves deprotonation, Michael addition, and nucleophilic substitution and features readily available materials, good to excellent yields, diastereospecificity, atom and step economy, wide substrate scope, easy separation, and mild conditions.
Keyphrases
  • ionic liquid
  • molecular dynamics
  • liquid chromatography
  • mass spectrometry
  • visible light
  • amino acid