Catalytic asymmetric homo-aldol reaction of pyruvate—a chiral Lewis acid catalyst that mimics aldolase enzymes

Abstract

The first catalytic asymmetric homo-aldol reaction of ethyl pyruvate leading to diethyl-2-hydroxy-2-methyl-4-oxoglutarate in up to 96% enantiomeric excess is reported; this reaction has been investigated for various catalysts, amines and solvents, and it is demonstrated that this new reaction leads to a simple synthetic procedure for the formation of optically active isotetronic acid derivatives.