Mukaiyama Aldol Reaction Of Indirubin-Derived β,γ-unsaturated α-ketone Ester And Enol Silicone Ether Catalyzed By Copper

The Mukaiyama aldol reaction is a reaction in which carbon-carbon bonds are formed between carbonyl compounds and enolsilanes,through which the β-hydroxyl carbonyl compounds can be formed.This approach is one of the most widely used methods for constructing complex organic molecules in a stereoselective manner.Due to the wide existence of indirubin skeleton structure in various drug molecules and active substances,the asymmetric neighborhood studies on indirubin have been numerous in recent years.However,as the derivatives of indirubin,β-γ-unsaturatedα-ketone esters have both the basic skeleton structure of indirubin and the important structural unit of unsaturated ketone esters,so there are few studies on the reaction between using it as the starting substrate and enolsilanes.The origin of the paper the first part introduces the Mukaiyama aldol reaction and subsequent researchers used catalytic reaction type of expanding,including chiral lewis acid catalysis,chiral boron complex catalysis and chiral metal box or pybox complex catalysis,chiral catalysis and chiral lewis base organic molecules mediated activation of lewis acid catalysis,etc.Then,the structure of β-γ-unsaturated α-ketone ester derived from indirubin was introduced,and the current research work onβ-γ-unsaturated α-ketone ester was reviewed.In the second part of the thesis,the author mainly describes in detail the subject proposal and design,the selection of model reaction,the final optimization of ligand,the optimization and determination of various reaction conditions,the expansion and amplification experiments of substrates,the determination of the absolute configuration of substrates and the possible catalytic model.Under the catalysis of cheap and easily available common metal copper,the reaction took place smoothly,and with excellent yield and enantioselectivity,a variety of chiral β-hydroxyl carbonyl compounds containing indigo framework were obtained.The reaction conditions were mild and simple,and could be successfully amplified by dozens of times.In the third part of the paper,the instruments and drugs involved in the experiment and the synthesis steps of the compounds are described in detail,and the spectral data and experimental characterization data of the new compounds involved in the experiment are provided.