2002 Fiscal Year Final Research Report Summary
Creation of Enantioselective Cross- Coupling Reactions in the Solid State
| Project/Area Number |
13640595
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
物質変換
|
|---|
| Research Institution | OKAYAMA UNIVERSITY OF SCIENCE |
|---|
Principal Investigator |
TODA Fumio OKAYAMA UNIVERSITY OF SCIENCE Department of Chemiatry, Professor, 理学部, 教授 (50036232)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
TOYOTA Shinji OKAYAMA UNIVERSITY OF SCIENCE Department of Chemiatry, Professor, 理学部, 教授 (80207646)
|
|---|
| Project Period (FY) |
2001 – 2002
|
| Keywords | cross-coupling reaction / enantioselective reaction / host-guest complex / solvent-free reaction / solid state reaction / tautomerism / monitoring by spectrum / analysis of reaction mechanism |
|---|
| Research Abstract |
Firstly, various organic neactions were carried out in the solid state in order to develop organic solid state reactions. When substrate and / or reagent is liquid, reaction between them was carred out under solvent-free conditions. Sililation reaction of alcohols proceeded efficriently just by mixing of alcohol and trialkylsilyl chloride. Claisen, Thorpe and Cannizzaro reactions were also found to proceed efficiently under solvent-free conditions. Cross-Claisen and Thorpe reactions were also successful. By monitoring of a solvent-free Thorpe reaction by continuous measurements of IR spectra, reaction intermediate was detected and reaction mechanism was clarified. Real solid state reaction is also effective. For example, FeCIa-catalyzed coupling reaction of 2-naphthol proceeded in the solid state very efficiently and its dimer 2, 2' -dihydroxy- 1, -binapthyl was obtained in good yield. However, coss-coupling reaction of 2-naphthol and 1, 2 -naphthalenediol in the solid state gave a complex mixture. Inclusion complexation of two different guest molecules by a host to give an interesting complex consisted of three different components. Unfortunately, however, cross-coupling reaction of the two tautomers was unsuccessful. When chiral host is used for such the cross-coupling reaction in the solid state, enantioselective solvent-free cross-coupling reaction can be accomplished. We are going to design such the dreamy reaction
|
