Chemoselective Transformation of C-C Double Bonds by Using Transition-Metal Hediated Electrolysis
| Project/Area Number |
08651011
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
有機工業化学
|
|---|
| Research Institution | Okayama University |
|---|
Principal Investigator |
KUROBOSHI Manabu Okayama University, Faculty of Engineering, Lecturer, 工学部, 講師 (30242316)
|
|---|
| Project Period (FY) |
1996 – 1997
|
| Project Status |
Completed (Fiscal Year 1997)
|
| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1997: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
|
|---|
| Keywords | Olefin / Oxidation / Electrolysis / Ruthenium / Osmium / Asymmetric Induction / Natural Product / ジヒドロキシル化 / アミノヒドロキシル化 |
|---|
| Research Abstract |
In this project were investigated dihydroxylation and aminohydroxylation of carbon-carbon double bonds using transition-metal catalysts.
Chiral diols were obtained from asymmetric electro-dihydroxylation of olefins using osmium and chiral ligands in the presence of a catalytic amount of potassium ferricyanide or iodine. This method was applied to the synthesis of chiral Shikonin. Effects of intramolecular hetero-atom on chiral induction was also studied.
N,N-Dichloro-p-toluenesulfonamide was obtained from electrolysis of p-sulfonamide in aq. NaCl. The dichlorinated sulfonamide was easily hydrolyzed with a basic aqueous solution to give N-chloro-p-toluenesulfonamide. Asymmetric aminohydroxylation of olefins using the chlorinated p-toluenesulfonamide in the presence of chiral osmium catalyst proceeded smoothly to give chiral aminols in moderate yields and ees.
|
Report
(3 results)
Research Products
(13 results)
