Cleavage of esters under nearly neutral conditions at high pressure

Abstract

Abstract Hydrolysis of esters proceeded at room temperature under high pressure in the presence of iPr2, NEt or N-methylmorpholine using CH3CN—H2O (60:1) as the solvent. This very mild procedure enables the smooth hydrolysis of biologically important compounds such as amino esters, aliphatic unsaturated fatty esters, and β-hydroxy ester; no racemization, no isomerization, and no side reactions take place. Selective hydrolysis of two ester groups is also accomplished with alcohol exchange reactions. This new synthetic technique can be utilized for the mild and selective hydrolysis of sophisticated molecules. Hydrolysis of esters is one of the most essential transformations in organic synthesis. Normally, a basic or acidic aqueous solution is used for ester hydrolysis. However, the hydrolysis of biologically related molecules such as amino esters, peptides, …, or unstaturated fatty esters, under such conditions is accompanied by side reactions, loss of chirality, or isomerization.1 We report an entirely new...