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The Synthesis Of Chiral Phase Transfer Catalyst And Its Application In Asymmetric Synthesis

Posted on:2003-06-19Degree:MasterType:Thesis
Country:ChinaCandidate:Y X HuaFull Text:PDF
GTID:2191360062995864Subject:Organic Chemistry
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Asymmetric synthesis using chiral phase transfer catalyst is a new method that has just been developed in late years. The aim of this thesis is to synthesize some new chiral quaternary ammonium salts and bis-quaternary ammonium salts from the popular material------Chloramphenicoland abietic acid, and then we used these chiral quaternary ammonium salts in some substitution reactions and addition reactions in order to research their catalytic action and asymmetric induction.Followings are the main work of this thesis:1. It summarized the development and the recently research work onusing chiral quaternary ammonium salts as phase transfer catalyst in these?years.2. Using Chloramphenicol as beginning material, by the reaction of hydrolysis, neutralization, dimethylation and quaternarization, we get two new chiral quaternary ammonium salts as phase transfer catalyst : PTC-la andPTC-lb.3. Using abietic acid as beginning material, by the reaction of deoxidize, substitution and quaternarization, we get two new chiral quaternary ammonium salts as phase transfer catalyst : PTC-lc and PTC-Id.4. Using Chloramphenicol as beginning material again, we get twonew chiral bis-quaternary ammonium salts as phase transfer catalyst: PTC-2a and PTC-2b by the reaction of hydrolysis neutralization, dimethylation and bis-quaternarization.5. All the chiral quaternary ammonium salts synthesized and their intermediates were analyzed and characterized by !H-NMR> IR^ MS and Elemental Anal.6. In order to study the catalysis and asymmetric induction of these chiral quaternary ammonium salts, we used them as phase transfer catalyst in the reaction of addition and the substitution.7. A mode for the asymmetric induction of the chiral phase transfer catalyst was suggested on the basis of the results of the experiment and the relate theory.
Keywords/Search Tags:Asymmetric synthesis, chiral quaternary ammonium salt, chiral bis-quaternary ammonium salt, phase, transfer catalyst
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