Activity and enantioselectivity in the hydrolysis of substituted phenyl esters catalysed by imidazole‐containing poly(iminomethylenes)

Abstract

Abstract The hydrolysis of achiral and chiral esters by optically active poly(iminomethylenes), [R‐NC<] n , which contain imidazole groups in their side chains R , has been studied. The polymers include poly(L‐ and D‐carbylalanyl‐L‐histidine), 2d and 2e , poly(D‐carbylalanyl‐L‐histidinol), 2f , and poly(L‐carbyl‐α‐methylhistamine), 1c . The esterolytic catalytic activity of the polymers towards neutral and charged esters increases in the series 2d, 2e >> 1c < 2f . Poly(D‐carbylalanyl‐L–histidinol) shows enantioselectivity in the hydrolysis of p ‐nitrophenyl esters of D‐ and L‐amino acids, k L / k D = 1.1.