Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis

Wei Liu, Siraj Z. Ali, Stephen E. Ammann, M. Christina White

Research output: Contribution to journalArticlepeer-review


We report the development of Pd(II)/cis-aryl sulfoxide-oxazoline (cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic olefins. We anticipate that this new chiral ligand class will find use in other transition metal catalyzed processes that operate under oxidative conditions.

Original languageEnglish (US)
Pages (from-to)10658-10662
Number of pages5
JournalJournal of the American Chemical Society
Issue number34
StatePublished - Aug 29 2018

ASJC Scopus subject areas

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


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