Research On Construction Of Spiro-oxindole Compounds By Chiral Tertiary Amine-catalyzed Asymmetric Tandem Reactions

In recent years, organocatalytic tandem reactions as effective methodsfor the synthesis of chiral compounds, have become a hot research topic.Among the several different catalytic systems, chiral tertiaryamine-catalyzed asymmetric cascade reactions have achievedunprecedented development. spiro-oxindole skeleton is the ubiquitousstructure of many pharmacologically active molecules, Theskeleton-containing compounds are the aimed products of many drugsand organic chemists. So, the development of asymmetric catalyzedtandem reaction to construct spiro-oxindole compounds is of greatsignificance. This thesis briefly describes the development of tertiaryamine-urea/thiourea catalysis, and then summarized the syntheticmethods of spiro-oxindole compounds via asymmetric tandem reaction.Inspired by these achievements,, we developed a one-potthree-component of isatin, malonontrile and3,4-hexanedione via aKnoevenagel-Michael-Aldol cascade reaction to form a five-membered ring, good yield and stereoselectivity was obtained;The asymmetric Aldol-Hemiketalization domino reaction with isatin and3,4-hexanedione in the promotion of chiral tertiary amine was alsoexplored, good yield and stereoselectivity was achieved, but instability ofthe desired product affect our in-depth study.In summary, we studied two different kinds of asymmetric tandemreactions catalyzed by chiral tertiary amine to synthesize spiro-oxindolecompounds with several chiral centers. They both acheived goodstereoselectivity. our asymmetric methodologies have several advantages,such as using cheap and facile material, having high stereoselectivitily,etc., thus have potential theoretical significance and application value.