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Studies Toward the Asymmetric Claisen Rearrangement of Flavonoids

Author: BaiXiaoHui
Tutor: WangSongQing；LeiXiaoGuang
School: Tianjin University
Course: Medicinal Chemistry
Keywords: Sanggenon C Flavonoids Asymmetric Claisen rearrangement reactions Chiral Bronsted acid Hydrogen bonds
CLC: O643.32
Type: Master's thesis
Year: 2010
Downloads: 110
Quote: 0
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Abstract


Sanggenon C is a kind of flavonoids , anti-inflammatory and antihypertensive effect in rats , the present study aims to Sanggenon C asymmetric total synthesis of , its inverse synthetic route shows Claisen the rearrangement reaction is a key step in the asymmetric synthesis process . According to the literature , chiral Bronsted acid catalyzed Claisen rearrangement reaction , so finding the right catalyst to improve the activity and selectivity of the reaction has become the main research contents of this experiment . The experiment synthetic template compound - 3 - allyl - substituted flavonoids and its substrate for the study of reaction conditions ( reaction time, temperature , catalyst , solvent , etc.) methodological studies to be more good reaction yield and selectivity on the basis of different substrates , and will eventually the mature experimental methods applied to the asymmetric synthesis of the the natural compound Sanggenon C . After experiment shows : 3 - allyl - substituted flavonoids easier synthesis, in its substrate asymmetric Claisen rearrangement reaction , try the chiral BINOL and its derivatives as a ligand , boron alkyl formed as a Lewis acid catalyst and template substrate carbonyl and hydroxyl hydrogen catalytic form of the complex transition state , and achieved certain results in the course of the experiment ; also tried catalyzed by palladium, copper and other metals and other more kinds of catalytic form , were not to be satisfied with the results, decided modified BINOL as a ligand for asymmetric catalytic reactions . Literature search , the experimental design of several expected to get better reactivity and selectivity BINOL derivatives synthesis and the study of the activity and selectivity . Sanggenon C has not been fully reported in the literature synthesis route on the hydrogen bond complex catalyzed asymmetric Claisen rearrangement reaction is rarely reported in the literature , is a cutting-edge research content . The subject of asymmetric Claisen rearrangement the response and Sanggenon C asymmetric synthesis has a very important significance .

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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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