A Novel Synthesis of Highly Branched-Alkyl Aryl Ketones Using the Conjugate Addition of the Gilman Lithio Cuprate to (beta)-Methylthio-(alpha),(beta)-unsaturated Ketones: Abnormal Reactivity of the Intermediary Enolates toward Molecular Oxygen

In order to synthesize highly branched-alkyl aryl ketones, l-(methylthio)-1-alken-2-yl phenyl ketones were subjected to the reaction with lithium dialkylcuprate. The high reactivity of an intermediary enolate toward molecular oxygen was found to give (alpha)hydroperoxy ketones.