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Chiral Supramolecular Catalyzed Asymmetric Mannich Reaction And Its Application In The Synthesis Of Dapoxetine

Posted on:2017-10-12Degree:MasterType:Thesis
Country:ChinaCandidate:G J PanFull Text:PDF
GTID:2481304880957049Subject:Chemical Engineering and Technology
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Asymmetric organocatalytic Mannich reaction was always one hot domain in research.The products were the intermediate compounds which may construct many nitrogenous chiral drugs.While there were still some limitations especially in catalysis performance and versatility on the reported catalysts so far.Therefore,it was important to seek better performance catalysts which could be used in the industrial production.In recent years,supramolecular chiral catalysts asymmetric reactions exhibited good catalytic performance and drew more and more researchers' attention.Thus,this dissertation included the following three parts:(1)A comprehensive overview of small molecule catalytic asymmetric Mannich reaction.(2)The study demonstrated that a new kind of chiral supramolecular organocatalyst,self-assembled by PPG1000 with proline via non-covalent bond,was disclosed.Furthermore,highly efficient asymmetric organocatalytic performance was shown in Mannich reaction between N-Boc aryl imine and aldehyde containing (?)-H with high yields(up to 95%),excellent diastereoselectivities(up to 99:1)and excellent enantioselectivities(up to 99%ee).The formation mechanism of the chiral supramolecular catalyst was further confirmed by ESI-MS method.(3)The designed chiral supramolecular catalyst was successfully applied to synthetize Dapoxetine.The yield of the key generating chirality step increased to 59% compared to the 50% yield catalyzed by proline.While the seven-step total yield was 27%(benzaldehyde as original reactant)and enantiomeric excess was 99%.
Keywords/Search Tags:Mannich reaction, asymmetric catalysis, chiral supramolecular catalyst, Dapoxetine
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