Synthesis Of Ligands Of Chiral Catalysts Of 1,3-Dipolar Cycloaddition Reaction

The 1,3-dipolar cycloaddition reaction is the most useful reaction in fundmental theory of organic chemistry and organic synthesis. The studies indicate that 1,3-dipolar cycloaddition reactions are concerted reactions. The most 1,3-dipolar cycloaddition reactions have well regioselectivity. So the works focus on the study of stereoselectivity. The reaction of achiral dipolar reagents and achiral alkenes may have well stereoselectivity by applying one effective chiral metal catalysts. So 1,3-dipolar cycloaddition reactions catalyzed by chiral metal catalysts become one of study hotspots in organic synthesis today. The article studied the chiral ligands of chiral metal catalysts in 1,3-dipolar cycloaddition reaction. We design a series of chiral ligands in which the chiral α-amino acid is chiral source. These ligands conclude the derivatives of α-amino acyl phenol, α-amino acyl naphthol and α-amino acyl-1,1'-binaphthalene-2,2'-diol. They have well ability of coordination. Here, we synthesize the derivatives of α-amino acyl phenol. The paper mainly synthesized three kinds of α-amino acid esters by the high performance catalysts of DMAP and DCC. The α-amino acid esters conclude L-Phenylglycin N-(p-methyl phenylsulfonyl)-4-methylphenyl ester, L-Alanine N-[(phenylmethoxy) carbonyl]-4-methylphenyl ester and L-Phenylalanine N-[(phenylmethoxy) carbonyl]-4-methylphenyl ester. This method is simpler and quicker than the traditional method. Furthermore, the side reaction is little and the process of disposal is easy. Otherwise we synthesize acetyl-4-methylphenyl ester and accomplished its Fries rearrangement reaction .