| Project/Area Number |
63470013
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
NAKAMURA Eiichi Tokyo Institute of Technology ; Faculty of Science ; Associate Professor, 理学部, 助教授 (00134809)
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| Project Period (FY) |
1988 – 1990
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| Project Status |
Completed (Fiscal Year 1990)
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| Budget Amount *help |
¥7,200,000 (Direct Cost: ¥7,200,000)
Fiscal Year 1990: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1989: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1988: ¥4,100,000 (Direct Cost: ¥4,100,000)
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| Keywords | Cycloaddition / Tetrahydrofuran / Dicarbonyl compounds / Cyclopropene / Asymmetric synthesis / Five-membered rings / テトラヒドロフラン / シクロプロパノン / シクロプロペノン / 歪み化合物 / ラクトン / 超高圧反応 / シクロペンタン / トリメチレンメタン |
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| Research Abstract |
Aim of the Research : This program is directed toward the development of new reactive intermediates and new reactions by taking advantage of the internal chemical energy stored in strained molecules.
Results : The following three reactions have been developed. (1) New thermal [3+2] cycloaddition. The reaction of 2, 2-dialkoxy-1-methylenecyclopropane with electron-deficient olefins under mild thermal conditions gives cyclopentanes in high yield. A similar reaction with carbonyl compounds affords substituted tetrahydrofurans. The mechanism and the nature of the reactive intermediate have been elucidated by kinetic and theoretical studies. (2) Carbometalation reaction. Addition of organometallics to cyclopropenone acetals provided a new entry to the chemistry of cyclopropyl metal compounds, which was further applied to the asymmetric synthesis of optically active compounds. (3) Synthesis of dicarbonyl compounds. Palladium-catalyzed reaction of cyclopropanone acetals with aryl triflates in the presence of carbon monoxide provided a new entry to the synthesis of 1, 4-dicarbonyl compounds.
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