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Three-component Reaction Based on Trapping Ammonium Ylide and Synthesis of Two Functional-organic Moleculars
Author: DiChangWei
Tutor: HuWenHao
School: East China Normal University
Course: Organic Chemistry
Keywords: Ammonium ylide Three-component reaction Diastereoselectivity Asymmetry Functional organic molecules Study on the Synthesis
CLC: O621.3
Type: Master's thesis
Year: 2010
Downloads: 17
Quote: 0
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Abstract
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Ylides organic reactions in the class of reactive intermediates the traditional ylides reaction has been widely used in organic synthesis . May be made of the simple structure of the compound through the multi - component reaction fast, efficient, high atom economy of the structural complexity and diversity of the product , is closest to the ideal concept of synthetic . This paper introduces a class -based capture lively ylide intermediates novel multi-component reaction . We found that the ketone compounds of the the lively ammonium ylide capture , of copper ( II ) catalyzed by diazo acetate , aromatic amines and β, γ- unsaturated keto ester multicomponent reaction . Explore optimal reaction conditions for this type of reaction , the influence on the reaction of the different reaction components , through the regulation of the various reaction components electronic effects and steric substituent to achieve better control of product diastereoselective . We also studied the mechanism of the reaction , reaction control through two sets of points , excluding amine epoxy compound intermediates may open loop demonstrated the correctness of the of the ketoesters lively ammonium ylide intermediates capture mechanism . We do attempt to asymmetric catalysis , although the results are not ideal , but also indicates the possibility . 1 - cyclobuten - 1 ,2 - dimethanol and 1 - cyclobuten - 1 ,2 - two carboxylate precursor is important in many synthetic intermediates . Optimized synthesis process , the success achieved in the laboratory - cyclobutene -1 ,2 - methyl formate kg scale synthesis .
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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry
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