Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

Stephen E. Ammann, Wei Liu, M. Christina White

Research output: Contribution to journalArticlepeer-review

Abstract

The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92 % ee, 13 examples with greater than 90 % ee).

Original languageEnglish (US)
Pages (from-to)9571-9575
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number33
DOIs
StatePublished - 2016

Keywords

  • C−H activation
  • S ligands
  • asymmetric catalysis
  • oxidation
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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