Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols

Nicholas J. Race, Cristiane S. Schwalm, Takayuki Nakamuro, Matthew S. Sigman

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

An enantioselective intermolecular coupling of oxygen nucleophiles and allylic alcohols to give β-aryloxycarbonyl compounds is disclosed using a chiral pyridine oxazoline-ligated palladium catalyst under mild conditions. As opposed to the formation of traditional Wacker-type products, enantioselective migratory insertion is followed by β-hydride elimination toward the adjacent alcohol. Deuterium labeling experiments suggest a syn-migratory insertion of the alkene into the Pd-O bond. A broad scope of phenols, various allylic alcohols, and an alkyl hydroperoxide are viable coupling partners in this process.

Original languageEnglish (US)
Pages (from-to)15881-15884
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number49
DOIs
StatePublished - Dec 14 2016

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