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Novel Chiral Ligand Catalytic Asymmetric Micheal Reaction

Posted on:2013-07-27Degree:MasterType:Thesis
Country:ChinaCandidate:T XuFull Text:PDF
GTID:2231330371477113Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
2,2’-Dihydroxy-1,1’-binaphthalene(BINOL,1),2,2’-Diamino-1,1’-binaphthalene (BINAM,2) and 2-Amino-2’-hydroxy-1,1’-binaphthyl (NOBIN,3) are similar interms of their functionality and scaffold. Since Kocovsky first reported the synthetic method for 3, the chemistry of 3 has been developed rapidly. Various chiral ligands could be easily obtained by simple transformation from 3. Their application in various asymmetric reactions, such as diethyl zinc addition to aldehydes, allylation of aldehydes, cyclopropanation, Suzuki coupling reactions, made clear that 3 has become one type of fine scaffold for construction of various chiral ligands for asymmetric catalysis.This article using 2-acetonaphthone as material, via oximate、Beckmann rearrangment、hydrolysis, obtained 2-aminonaphthalene. Racemic 3 can be synthesized through coupling of 2-aminonaphthalene and 2-naphthol. Synthesis of enantiopure 3 through optical resolution. Enantiopure 3 react with 2-Hydroxy-5-methyl-1,3-benzenedicarboxaldehyde producing a novel ligand 4.Chalcone have anti-inflammatory, sterilization efficacy, so the research about chalcone is a very important issue in medicine and other fileds. Because chalcone has important function in medicine filed, the research about its chiral derivatives has important significance. Asymmetric Michael reaction about chalkone is the important method to introducing the C-C bond, C-N bond and C-O bond when synthesis of chiral compounds or heterocyclic...
Keywords/Search Tags:axial chirality, NOBIN, chiral ligand, asymmetric catalysis, Michaelreaction, chalcone
PDF Full Text Request
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