| Project/Area Number |
19590018
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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 |
Chemical pharmacy
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| Research Institution | Tokyo University of Science |
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Principal Investigator |
SATOH Tsuyoshi Tokyo University of Science, 理学部, 教授 (20089329)
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| Project Period (FY) |
2007 – 2009
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| Project Status |
Completed (Fiscal Year 2009)
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| Budget Amount *help |
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2008: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2007: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | カルベン / カルベノイド / 有機マグネシウム化合物 / スルホキシド / マグネシウムカルベノイド / 有機合成 / 不斉合成 / スルホキシド-マグネシウム交換反応 / 有機マグネシウム / スルホキシドーマグネシウム交換反応 / 有機合成反応 / グリニヤール試薬 / シクロプロピルイヒ / 1.3-CH挿入反応 / ホモロゲーション |
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| Research Abstract |
Carbenes and carbenoids have long been known to be highly reactive carbon species that show a variety of unique reactivities. However, those reactive species are not fully used in organic synthesis. The reasons are as follows : one is the precursors for the generation of carbenes and carbenoids are quite limited and the other is that the reactivity of the species is too high to control. In order to solve the problem mentioned above, we used α-haloalkyl (or alkenyl) aryl sulfoxides as the precursors and used sulfoxide-magnesium exchange reaction for generation of much mild magnesium carbenoids. α-Haloalkyl (or alkenyl) aryl sulfoxides are quite easily synthesized in high overall yields. Magnesium carbenoids, cyclopropylmagnesium carbenoids, cyclobutylmagnesium carbenoids, magnesium β-oxido carbenoids, and magnesium alkylidene carbenoids are generated at low temperature from the corresponding sulfoxides with a Grignard reagent in quantitative yields. They were found to be stable usually at below -60℃ for at least 30 min. The each magnesium carbenoids have their own unique reactivities and we could found many unprecedented reactions from these reactive species.
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