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 language | English (US) |
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Pages (from-to) | 15881-15884 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 138 |
Issue number | 49 |
DOIs | |
State | Published - Dec 14 2016 |
Externally published | Yes |
Bibliographical note
Publisher Copyright:© 2016 American Chemical Society.