The Catalytic Asymmetric Michael Addition Of3-hydroxyoxindole To α,β-unsaturated Carbonyl Compound Catalyzed Semi-azacrown Ether Ligand

It is well known that3-hydroxyoxindole has the potential to be a Michaeladdition donor. These corresponding products,3,3-disubstituted oxindoles, are notonly a useful structural motif found in many natural products, but also attractivetargets because of their promising biological activities. In this thesis, we havecommitted ourselves to research on the asymmetric Michael addition of3-hydroxyoxindole to α,β-unsaturated esters or α,β-enones catalyzed by chiralsemi-aza-crown ligand. We completed the following two significant tasks：1. The catalytic asymmetric Michael addition of3-hydroxyoxindole toα,β-unsaturated esters in presence of a catalytic amount of chiral semi-azacrownether ligand.We developed the asymmetric Michael addition of3-hydroxyoxindole toα,β-unsaturated esters, which is catalyzed by chiral semi-aza-crown ether ligand. Ourstudies commenced with experimental conditions such as reaction temperature,solvent, additive and substrate, because they affect the result of the asymmetricaddition. It was found that at the optimized conditions, the asymmetric addition canafford a range of3,3-disubstituted oxindoles bearing adjacent quaternary-tertiarycenters in good results (up to97%yield,24:1dr, and99%ee)2. The catalytic asymmetric Michael addition of3-hydroxyoxindole toenones in presence of a catalytic amount of chiral semi-azacrown ether ligand.We developed the asymmetric Michael addition of3-hydroxyoxindole to enones,which is catalyzed by chiral semi-aza-crown ether ligand. Our studies commencedwith experimental conditions, which affect the result of the asymmetric addition.They included reaction temperature, solvent, additive and substrate. It was found thatat the optimized conditions can afford a range of3,3-disubstituted oxindoles bearingadjacent quaternary-tertiary centers in excelent results (up to99%yield,1:1dr, and99%ee)...