Synthesis And Application Of Axis Chiral BINOL Amide Catalysts In Divinyl Ketones And Oxindoles Reaction

Over the past decade,small molecular organocatalysis is the fastest development direction in the field of asymmetric organocatalysis,and compared with asymmetric metal organic catalysis（three scientists in this field won Nobel Prize in chemistry in 2001）and asymmetric enzyme catalysis,asymmetric organic catalysis has received adequate attention of science researchers.Asymmetric organic catalysis can meet the activity and selectivity required in most of symmetric organic reaction,which becomes an important tool for the synthesis and construction of complex chiral organic molecular cytoskeleton,widely used in fields of chemistry,medicine,pesticides,biology,materials and so on.Therefore,it is still the focus in the field of asymmetric catalysis research to design and synthesize new chiral catalyst.The binaphthalene skeleton with axis chiral ligand is one of the most widely used and concerned chiral skeletons in asymmetric catalytic studies and can be applied to asymmetric synthesis as a good chiral inducer.This paper uses environmentally friendly,nontoxic,and inexpensive3-hydroxy-2-naphthoic acid as raw material and obtains（R）-2,2’-dihydroxy-1,1’-dinaphthyl-3,3’-dicarboxylic acid by ways of esterification,coupling,degreasing and separation of racemate compound.Based on multi hydrogen bond activation mode,through the binding of BINOL acid in R-configuration to chiral primary amine,nine kinds of axis chiral BINOL amide organic small molecular catalyst with hydrogen bond donor are synthesized,and synthesized axis chiral BINOL amide catalysts were characterized by ¹H NMR,¹³C NMR,HRMS,IR,melting point,which also achieves better catalytic effect when applied to the reaction of divinyl ketones and oxindoles in the best condition（40℃,CH₂Cl₂ as solvent,and Boc-D-Phg-OH as cocatalyst）.The obtained products were characterized by ¹H NMR,¹³C NMR,IR,melting point.The compound is an important indole derivatives,and has a certain biological activity,this providing an effective way for the development of drug molecules.