Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

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.

SUBMITTER: Race NJ 

PROVIDER: S-EPMC5180452 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature