1.
J Am Chem Soc
; 138(49): 15881-15884, 2016 12 14.
Artigo
em Inglês
| MEDLINE
| ID: mdl-27960316
RESUMO
An enantioselective intermolecular coupling of oxygen nucleophiles and allylic alcohols to give ß-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 ß-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.