Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

A chemodivergent copper-catalyzed ring opening of cyclokettoe oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of gamma- and delta-acyloxylatect alkoxylated, and hydroxylated nitrites while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxinie also proceeded well under the established conditions.