A general regio- and stereoselective gamma-C-C bond formation is achieved using alpha-halocarbonyl compounds and dienol ethers via Cu(II) catalysis. This method constitutes a novel approach to the challenging 1,6-dioxygenation motif. A range of gamma-substituted enones, including many bearing all-carbon quaternary centers, are available through a simple protocol under mild reaction conditions with superb functional group compatibility. Excellent stereoinduction is observed providing controlled access to challenging stereochemical arrays.