Biomimetic Chiral Pyridoxal and Pyridoxamine Catalysts

Vitamin B-6 serves as universal co-enzymes in biological systems. However, its catalytic power has not been applied into the area of asymmetric catalysis. Based on the core structure of vitamin B-6, we have developed several types of pyridoxal and pyridoxamine catalysts with different structural skeletons and different electronic properties. With these pyridoxals and pyridoxamines as catalysts, we have realized biomimetic asymmetric transamination of alpha-keto acids and biomimetic asymmetric Mannich reaction of glycinate, respectively, to give various chiral alpha-amino acids and alpha,beta-diamino acids in good yields with excellent diastero- and/or enantioselectivities. Both of the reactions have perfectly mimicked the corresponding biological transformations.