Lewis acid mediated selective monohydrolysis of geminal diesters: Synthesis of functionalized malonic acid half esters

摘要

Geminal diesters, N-alkyl/aryl-2,2-bis(ethoxycarbonyl)vinylamines, were found to undergo selective hydrolysis in the presence of BF 3· OEt 2 at room temperature to give the corresponding half esters. Neighboring group participation by nitrogen in the hydrolysis was observed. This method is useful for the preparation of highly functionalized malonic acid half esters.