1997 Fiscal Year Final Research Report Summary
Regio-and Stereo-selective Cathodic Coupling of Ketone and Vinylsilanes
| Project/Area Number |
08651014
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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 | Kinki Uneversity |
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Principal Investigator |
SHONO Tatsuya Institute for Science and Engineering, Kinki University, Professor, 理工学総合研究所, 教授 (80025858)
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| Co-Investigator(Kenkyū-buntansha) |
KASHIMURA Shigenori Department of Metallurgy, Kinki University, Assistant Professor, 理工学部, 講師 (50152632)
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| Project Period (FY) |
1996 – 1997
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| Keywords | Electroreduction / Coupling / Silvl substituted olefin / Diol / Regioselectivity |
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| Research Abstract |
It has been found in this study that the electroreductive intermolecular coupling of ketone with vinylsilanes was found to afford gamma-trimethylsilyl alcohols in satisfactory yields. This reaction is highly useful in organic synthesis since gamma-trimethylsilyl alcohol is a key precursor for the synthesis of allyl alcohol and 1,3-diol. It was also found that the elecroreductive intermolecular coupling of ketone with ethoxydimethylsilyl substituted olefins afforded oxasilacyclopentanes with excellent yield. This reaction was found to be useful for the regioselective synthesis of 1,4-diols. Regioselectivity of the electroreductive intermolecular coupling of ketone with trimethylsilyl substituted allyl alcohol was found to be controlled by trimethylsily group and gave homoallyl alcohols through the Peterson elimination of hydroxyl group and trimethylsily group. In the intramolecular coupling of ketone with vinylsilanes, the regioselectivity of the reaction was found to be controlled by trimethylsilyl group on the double bond and predominant formation of 6-membered ring product was observed.
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