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Studies on the Catalytic Asymmetric Methylation and Arylation of Nitrogen Heterocyclic Four Rings to Aldehydes

Author: MiaoPeiGuo
Tutor: HanQiao; WangMinCan
School: Zhengzhou University
Course: Organic Chemistry
Keywords: methylation diethylzinc dimethylzinc asymmetric catalysis arylation
CLC: O621.25
Type: Master's thesis
Year: 2012
Downloads: 21
Quote: 0
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Abstract


Nitrogen heterocyclic four rings chiral ligands were investigated in the paper, for catalytic asymmetric addition of dimethylzinc to aldehydes and its derivatives, and arylation of o-methanal benzoylbenzoate, the reaction has obtained the satisfactory results.1. The application of amino alcohol bearing two chiral centers in the asymmetric methylation.A pair of diastereoisomer were studied, in the condition of the chiral aziridino alcohol ligand L1(5mol%) and L2(5mol%) as catalyst, dimethylzinc and aldehydes were catalyted to get corresponding product in the asymmetric addition reaction, and finally found that they all have better catalytic efficiency. The results also show that, when the chiral ligands L1and L2were applied as catalyst severally, two different enantiomers were obtained.2. The discussion of chiral aziridino alcohol ligands in the catalytic asymmetric arylation of o-methanal benzoylbenzoate.Studying the asymmetric aryl reaction, in the presence of the diastereoisomer L1 and L2as catalyst, aryl boronic acid as aryl source and o-methanal benzoylbenzoate as substrate, The experimental results show they also have better catalytic efficiency. A catalytic amount (20mol%) of ligand L1and L2and aryl boronic acid were interacted by diethylzinc to o-methanal benzoylbenzoate, the highest92.5%of chemical production rate and96.2%of ee value were derived. Further study found that, by changing the corresponding of the structure of aryl boronic acid, a pair isomers of3-substitute phthalide were got.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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