Asymmetric Catalytic Reactions In Different Positions Of α,β-Unsaturated Carbonyl Compounds

The dissertation mainly focuses on the introduction of the selective functionalization of different positions of α,{-unsaturated carbonyl compounds (α,β-unsaturated y-butyrolactams,3-alkylidene oxindoles and maleimides) through asymmetric catalytic reactions.In the first part, by introducing the synthetic method of functionalization in the β-or γ-position of α,β-unsaturated carbonyl compounds, asymmetric Michael addition of a,b-unsaturated y-butyrolactams in the presence of (DHQD)2AQN and enantioselective vinylogous Michael addition of 3-alkylidene oxindoles catalyzed by bifunctional squaramide were achieved.In the second part, by introducing the selective functionalization in double position of α,β-unsaturated carbonyl compounds, diastereoselective DABCO-catalyzed cascade Michael-Aldol [3+2] annulation of maleimides and catalytic asymmetric Diels-Alder [4+2] annulation of α,β-unsaturated y-butyrolactams were achieved.We have developed some novel method of enantioselective functionalization in α-,β-or γ-position of α,β-unsaturated carbonyl compounds and corresponding products exhibited promising applications in chemical biology or drug discovery were obtained. The biological evaluation of these products and more studies on selective functionalization of α,β-unsaturated carbonyl compounds is currently underway by our group.