Next generation of Claisen condensation and related reactions: application to the syntheses of specific compounds
| Project/Area Number |
18K05133
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Kwansei Gakuin University |
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Principal Investigator |
Tanabe Yoo 関西学院大学, 理工学部, 教授 (30236666)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | クライゼン縮合 / 不斉クライゼン縮合 / 四塩化チタン / 四塩化ジルコニウム / 脱水型チタン=クライゼン縮合 / ホルミル化反応 / ドミノ反応 / フラノンアヌレーション反応 / α,β-不飽和エステル類 / 立体補完的・パラレル合成 / 医薬品合成への応用 / 多成分連結反応 |
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| Outline of Final Research Achievements |
The Claisen ester condensation is a well-recognized textbook chemistry. The concventional base-promoted reaction has been not fully exploited and the reactivity is generally poor, compared the relevant well-established aldol reactions. The Claisen ester condensations promoted by TiCl4 and ZrCl4 exhibits mild but higher reactivity. Moreover, crossed and asymmetric versions are possible. The author has been engaged in the subjects and has developed the longstanding studies.
During the course of this Grant-in-Aids for Scientific Research, we have developed the dehydration-type Claisen ester condensation, asymmetric Claisen-aldol tandem reaction, furanone annulation, and the relevant and synergistic project for stereocomplementary and parallel syntheses of multi-substituted (E)-, (Z)-stereodefined α,β-unsaturated esters using the obtained β-ketoesters or α-formylesters: application to drug syntheses.
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| Academic Significance and Societal Importance of the Research Achievements |
Ti-Claisen縮合反応の一部は Organic Syntheses 誌に開発経緯のレヴューとともに再現性有る実験手法を掲載している．実際，Corey 教授(Omuralide analogue) や Merck 社（anti-MRSA医薬）にて本反応は活用された．Claisen縮合反応に関し本格的に取り組んでいるのは，国際的にも当研究室のみであり，この分野の先導的発展に寄与していると考えている．
加えて，得られた多様なβ-ケトエステル類を原料として，立体補完的三・四置換 (E)-,(Z)-α,β-不飽和エステル合成および医薬品合成への応用研究とリンクさせて，シナジー効果を発揮している．
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Report
(4 results)
Research Products
(15 results)
