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Synthesis of New Cinchona Alkaloids Derivatives Catalysts and Their Catalytic Reactions

Author: SongJiangQing
Tutor: ZhangShengYong
School: Fourth Military Medical University
Course: Medicinal Chemistry
Keywords: Alkaloid quaternary ammonium salt Phase transfer catalyst Synthesis Chiral
CLC: O643.32
Type: Master's thesis
Year: 2011
Downloads: 30
Quote: 0
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Abstract


In the present study a variety of catalytic asymmetric synthesis reaction , the chiral phase transfer catalysis with a simple operation , mild reaction conditions, the advantages of environmentally-friendly and easy to expand the scale of production . N - diphenylmethylene glycine tert - butyl ester in the presence of a chiral phase transfer catalyst to the substrate using different alkylating reagent can be synthesized by a variety of optically active α-amino acid . And other asymmetric catalytic reactions , the design the synthesis efficient phase transfer catalyst is the key to the research of such reactions . Through the analysis of the the cinchona alkaloid quaternary ammonium salt phase transfer catalyst structure-activity relationship catalytic principle , such catalytic activity by the catalyst space three-dimensional structure as well as the impact of replacing the electronic effect of the group . Under the guidance of this basic idea , researchers successively synthesized a series of efficient phase transfer catalyst . Paper studies as follows: 1 Synthesis of the alkylation reaction of the substrate N - diphenylmethylene glycine tert- butyl ester. 2 to be considered while considering the electron effect of the influence of steric hindrance by the introduction of a benzyl group, a 9-OH in the cinchona derivative synthesized four novel chiral phase transfer catalyst . Product characterization by 1H NMR, IR, melting point , specific rotation . 3 N - diphenylmethylene glycine tert - butyl ester as substrate investigated four catalytic activity and enantioselectivity , and reaction conditions were optimized , the chemical yield of up to 69% , the best stereoselective 90? 4 . Explore the synthesis of new recyclable catalyst for the AD reaction .

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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