Mild esterification and transesterification of carboxylic acids catalyzed by tetracyanoethylene and dicyanoketene dimethyl acetal

Article abstract of DOI:10.1246/cl.1997.55

A π-acid tetracyanoethylene (TCNE) and its derivative dicyanoketene dimethyl acetal (DCKDMA) were found to catalyze esterification of lauric acid with various types of alcohols. This method was successfully applied to methyl esterification of a variety of carboxylic acids including aromatic, α,β-unsaturated, α-hydroxy, and N-Cbz and N-Boc-protected α-amino acids without racemization at the range from room temperature to 60 °C. TCNE was also found to operate as a catalyst in transeslerification reaction of methyl laurate.