1997 Fiscal Year Final Research Report Summary
Chemoselective Transformation of C-C Double Bonds by Using Transition-Metal Hediated Electrolysis
| Project/Area Number |
08651011
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Okayama University |
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Principal Investigator |
KUROBOSHI Manabu Okayama University, Faculty of Engineering, Lecturer, 工学部, 講師 (30242316)
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| Project Period (FY) |
1996 – 1997
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| Keywords | Olefin / Oxidation / Electrolysis / Ruthenium / Osmium / Asymmetric Induction / Natural Product |
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| 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.
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