Bisindolemethane Compounds And Organic Small Molecule Catalyzed Synthesis Of Chiral Amines

The first part of this dissertation focuses on the development of the efficient synthetic protocol for the synthesis of unsymmetric bis(indoly)methanes using Lewis acid InBr3was identified as an efficient catalyst to promot the Friedel-Crafts reaction of indoles with3-indolyl-substituted phthalides in water or in dichloromethane in good to excellent yield. Preliminary biological experiments indicated that these compounds have shown excellent anti-Alzheimer’s Disease activity.In the second part, cinchona derivatives promoting asymmetric Mannich reaction ofn4-hydroxycoumarin with N-p-tolylsulfinylimine was investigated. Chiral amines bearing coumarin moiety were constructed in moderate to excellent yields with moderate to good enatioselectivities. The absolute configuration of the corresponding product was assigned by using ECD caculation.Thirdly, an organocatalyst-promoted asymmetric a-aminoxylation/aza-Michael/aldol consendation cascade was developed. Chiral1,2-oxazine derivatives were obtained in good yields (up to70%), excellent enatio-(>99%ee in all cases) and diastereoselectivities (up to>99:1d.r.) under mild conditions. Notably, a multi-functional chiral syn-1,4-amino alcohol derivatives could be readily prepared from the1,2-oxazine derivatives.In the last part, a dual-catalyst, mutil-components, one-pot domino reaction,(Michael/aza-Henry/hemiaminalization/dehydration) was investigated. Chiral tetrahydropyridine derivatives were obtained in good yields (up to90%) with higher enatio-(up to>99%ee) and diastereoselectivities (>99:1d.r. in all cases) for a broad substrate scope under mild conditions.