| Project/Area Number |
20590013
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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 Pharmacy and Life Science |
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Principal Investigator |
TAGUCHI Takeo Tokyo University of Pharmacy and Life Science, 薬学部, 教授 (00016180)
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| Co-Investigator(Kenkyū-buntansha) |
YANAI Hikaru 東京薬科大学, 薬学部, 助教 (10408685)
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| Project Period (FY) |
2008 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2008: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | 有機フッ素化学 / フルオロアルケン / ペプチドイソスター / トリフルオロメチル / トリフリル基 / 炭素酸 / アルキルアルミニウム / ペプチドミメチックス / トリフルオロメタンスルホニル / アルドール反応 / メイケル付加反応 / ブレンステッド酸 / ジフルオロケトン / トリフルオロアセトアルデヒド / フルオロオレフィン / ジフルオロメチレン / 塩化クロム / 向山-マイケル反応 / アミド配座異性 / シリルオキシフラン |
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| Research Abstract |
On the basis of characteristic features of fluorinated organic molecules our research project consists of the following two parts ; (1) development of versatile synthetic methods for organo fluorine compounds directed to medicinal chemistry and (2) new carbon acid chemistry toward efficient catalysis of common synthetic reactions. Concerning the former subject we have successfully achieved the following reactions : (1)Regio and stereoselective synthesis of fluorinated olefins through the defluorinative allylic alkylation of difluorohomoallylic alcohols by copper mediated Grignard reaction or by copper free alkylaluminium reaction, and the further elaboration for the preparation of the corresponding dipeptide isosteres. (2)An efficient preparation of 1-fluoroalkenyl ester utilizing low valent chromium chemistry and the investigation of their reactivity as double acylating reagents. (3)Preparation of α,α-difluoroketone derivatives through the unique reaction of trifluoroacetaldehyde N,O-acetals with alkyllithium reagents. In the latter subject, we found that tetrakis(1,1,3,3-trifluoromethanesulfonyl)propane works as an extremely effective catalyst for the carbon-carbon bond forming reactions of enol silyl ethers as nucleophiles with carobonyl compounds such as α,β-unsaturated ketones, α,β-unsaturated aldehydes and sterically hindered ketones.
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