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Study on the New Reaction of Enamines with Aryldiazoacetates
Author: ZhaoWeiJie
Tutor: ZuoMing；JiShunJun
School: Suzhou University
Course: Organic Chemistry
Keywords: Enamine Diazo compound Catalytic reaction gamma - keto ester Copper salt
CLC: O621.25
Type: Master's thesis
Year: 2005
Downloads: 123
Quote: 0
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Abstract
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Transition metal copper or rhodium complex catalyzed addition reaction of aryl diazo acetate and allyl amine , and does not produce the desired amino cyclopropane- product of gamma - keto ester , but produced in a high yield . We have investigated in detail the structure of the reaction solvent , catalyst , enamine , and aryl diazonium compound effect on the reaction . Trace analysis on the reaction process , which found that the initial product of the reaction is a substituted enamine , the enamine intermediate is hydrolyzed in the process by column chromatography on silica gel to generate a gamma - keto ester as a final product . According to the results of this experiment and the Mechanism of the Reaction of the diazonium compound is understood , we believe that the reaction mechanism of the enamine with the metal carbene first nucleophilic addition , and then the hydrogen migration process occurs , resulting enamine intermediate . We also tested the dual chiral rhodium and copper catalysts on the reaction , found that gamma - keto esters can be obtained in a high yield , but the reaction is not enantioselective This result is consistent we have proposed reaction mechanism . Also try using the initially formed enamine intermediate with some of the electrophilic reagent the concatenated reaction occurs , but it is possible to obtain the success .
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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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