The Addition Of Pyridine To Glycine Catalyzed By Glycine Ester

α,β-Diamino acids are elementary structural units of many natural products and key structural fragments of biologically active compounds. They have been obtained extensive applications in many areas such as medicinal chemistry and biochemistry. In recent years, its role has become more and more prominent. There are many methods for the synthesis of α,β-diamino acids, but most of methods need multiple steps and harsh reaction conditions. Hence, it is meaningful to develop new and efficient methods for the synthesis of α,β-diamino acids.In biological systems, primary amines such as glycine can undergo direct functionization of the α-amino C-H bond without protection of NH2 group in the presence of enzymes. For example, enzymatic aldol reaction of glycine with aldehydes affords β-hydroxy-α-aminoacids. The catalysis center of the enzymes is Vitamin B6. Vitamin B6 family includes pyridoxamine, pyridoxal, and their phosphate derivatives.Claisen-type addition of glycine or its derivatives to imines provides an efficient and highly attractive approach to synthesize various α,β-diamino acids. Inspired by biological aldol reaction, we image that a biomimetic Mannich reaction of glycine and imines might be developed by using appropriate pyridoxals as the catalystThe studies include the following three parts:(1) Design and synthesis of a series of pyridoxal derivatives and investigation of their applications in catalytic Mannich reaction of glycine with imines.(2) Optimization of reaction conditions including solvents, bases, the amount of the base, concentration, and temperature.(3) Substrate scope examination under the optimal reaction conditions.