Electrochemical, Manganese-Assisted Carbon-Carbon Bond Formation between β-Keto Esters and Silyl Enol Ethers.

The electrochemical carbon-carbon bond formation process between β-keto esters and silyl enol ethers was investigated utilizing manganese salts. The tricarbonyl compounds were generated in moderate to good yields under neutral conditions. Control experiments revealed that an electro-generated base at the cathode is important. Electroanalytical measurements with a Mn(TPA) complex suggested that the oxidation of the silyl enol ether is the first step in the oxidation process initiated by a corresponding Mn(IV) species.