Further insight into the mechanism of Heck oxyarylation in the presence ofchiral ligands

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Abstract

The Heck oxyarylation reaction to 3-benzyloxypterocarpan (15) has been studied in the presence of chiral phosphine ligands, a chiral ionic liquid and (+)-α.pinene. The observed small selectivities suggest that this reaction takes place through parallel pathways and the main pathway involves an achiral intermediate 11 where the chirality introduced by the chiral ligands is lost. Although practical asymmetric Heck oxyarylation to chiral pterocarpans could not be achieved, a convenient Heck-oxyarylation synthesis of rac-15 with (+)-α.pinene as ligand gave the highest yield reported to this type of reactions.

Original languageEnglish
Pages (from-to)69-76
Number of pages8
JournalArkivoc
Volume2003
Issue number5
Publication statusPublished - Dec 1 2003

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Keywords

  • Asymmetric Heck oxyarylation
  • Chiral ligand
  • Ionic liquid
  • Pterocarpan

ASJC Scopus subject areas

  • Organic Chemistry

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