Oxygen-Involved Oxidative Deacetylation of α-Substituted β-Acetyl Amides - Synthesis of α-Keto Amides

alpha-Substituted beta-acetyl amides could undergo CC bond cleavage to form alpha-keto amides when treated with copper(II) chloride (CuCl2) and boron trifluoride diethyl etherate (BF3OEt2) under an oxygen atmosphere. The yield can be increased by the addition of tert-butyl hydroperoxide which alone can also effect the reaction. The reaction provides a new protocol for the synthesis of alpha-keto amides.