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The Study on the Direct Asymmetric Aldol Reaction Catalyzed by Axially Chiry Primary Amine

Author: ZhuGongJian
Tutor: DaChaoShan
School: Lanzhou University
Course: Biochemistry and Molecular Biology
Keywords: Axially chirality Chiral primary amine Direct asymmetric Aldol reaction Organocatalysis CCl4
CLC: O643.32
Type: Master's thesis
Year: 2008
Downloads: 145
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Abstract


Organocatalysis have received great attention in asymmetric synthesis for its enzyme mimic, metal-free, atomatically economic and low toxic characters. In this dissertation we have designed and synthesized three novel axially chiry primary amine catalysts. Then the direct aldol reactions between aromatic aldehydes and ketones catalyzed by these catalysts have been studied in detail.In part I, three axially chiry primary amine molecules were synthesized using chirl BINOL and chiral diamines as main materials.In part II, the catalytic effects of organocatalysts to catalyze the direct asymmetric aldol reaction were evaluated. we have also optimized the catalyst, solvent, additive and temperature. The results indicated that high chemical yield (92%) , and good enantioselectivity (63% ee) were obtained when acetone reacted with electron - deficient aromatic aldehydes catalyzed by N, N’ - Bis [ (1 S, 2 S) - (2 -Amino) ] cyclohexyl - (S) - 2, 2’ - dihydroxy -1,1’- binaphthyl - 3, 3’ - dicarboxamides in CCl4 at the room temperature by adding benzoic acid.

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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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