Synthesis Of C₂-asymmetric Phase-transfer Catalytic And Application

Phase transfer catalytic reaction is a new field in asymmetric synthetical reactions, and it has following advantages:high yield,mild reaction condition and simple operation.A variety of new chiral phase transfer catalysts have emerged to this area and added the new vitality to it.There are two species of chiral phase transfer catalysts, including chrial crow ether.Chiral quaternary ammonium salts has been used widely. Chiral quaternary ammonium salts is also used in kinds of asymmetric phase-transfer catalytic reaction including the alkylation,Michael addition,aldol reaction,Mannich reaction,oxidation and reduction.In this paper,we studied the synthesis of chiral quaternary ammonium salts as phase-trasfer catalyst.And we researched its application in Michael addition reaction. The three parts are involved in the dissertation.In the first part,we synthesized a kind of C₂-asymmetric chiral quaternary ammonium salts which was prepared from L-proline as the starting material via amide, reduction of LiAlH₄ and alkylation.Sencond,chiral quaternary ammonium salts phase-transfer catalyst which was synthesized can be used in Michael addition reaction and optimize the reaction conditions.Farther,we studied the influence of kinds of different configuration ofα,β-unsaturated aldehyde and ketone in Michael addition reaction.In the third part,the complexes of diamine with copper acetate was made use of in asymmetric Henry reaction.Simultaneously,the reaction conditions was optimized.Kinds of different configuration of aldehyde was researched in optimal condition to Henry reaction.It has following advantages:high yield and mild reaction condition.In summary,the reactions mentioned above have advantages of mild reaction conditions,environmental benignity,easy to handle and simple manipulation and high yields.In this study,we designed a new kind of catalyst and it has a borad application in organic synthesis.