The Application of MCRs（Multicomponent Reactions）：The Modified Chiral ligands for Catalytic Asymmetric Synthesis and Fluorescence Senses

• Main Authors: Hung-Kai Fu, 傅虹愷
• Other Authors: guang-sheng sung
• Format: Others
• Language: zh-TW
• Published: 2005
• Online Access: http://ndltd.ncl.edu.tw/handle/08422769945197279991

碩士 === 國立成功大學 === 化學系碩博士班 === 93 === 　The study used U-4CR as a blueprint to design highly stereoselective multicomponent reactions, which are simple, convenient and changeful, so as to produce some chiral compounds. 　The multicomponent reactions involve mixing an isocyanide, aldehyde and amino acid in methanol. The reactions give chiral products with high optical purity. 　　The reaction is sensitive to the structure of aldehyde and amino acid. Usually the more bulky the substituents are the higher optical purities the products have. The researcher could use the synthetic method to design many chiral compounds and modify the compounds for his purposes by means of cyclization, alkylation and reduction. While modifying the structure of the compounds, it was amazing for the researcher to discover that tertiary amines, instead of quaternary ammonium salts, were obtained due to steric effects. 　During the reduction, ester could be easily reduced at the room temperature. However, the researcher found out that, in addition to reduction of ester to alcohol, amide was also reduced into amine under the mild conditions. At the same conditions, some other compounds couldn’t reach the same result. 　By multicomponent reactions, we could synthesize several compounds with different functions. After simple modification of structure, the chiral compounds we prepared may have some applications, such as (1)Application to catalytic asymmetric synthesis to the chiral compounds may serve as chiral ligands in catalytic asymmetric synthesis. (2)Application to organic fluorescent sensor: With the detective and indicative designs, the compounds became an organic fluorescent sensor having functions of detecting specific metallic ions. 　Some of the chiral compounds have correlated probe and indicator parts, which may generate on/off fluorescent signals.