Development of new tandem reactions by using bis(oxazoline) ligands
| Project/Area Number |
24590026
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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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| Research Field |
Chemical pharmacy
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| Research Institution | Toho University |
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Principal Investigator |
KATO Keisuke 東邦大学, 薬学部, 教授 (80276609)
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| Co-Investigator(Kenkyū-buntansha) |
KUSAKABE Taichi 東邦大学, 薬学部, 講師 (00600032)
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| Co-Investigator(Renkei-kenkyūsha) |
INOUYE Yoshio 東邦大学, 薬学部, 教授 (00136053)
KANNO Yuichiro 東邦大学, 薬学部, 講師 (40453849)
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | パラジウム / ビスオキサゾリン / カルボニル化 / CCC-coupling反応 / 5-メトキシ-3(2H)-フラノン / ジヘテロアリールケトン / ジアリールケトン / フラノン / カップリング / CCC-coupling / リガンド |
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| Outline of Final Research Achievements |
In our early work, we found that bis(oxazoline) (box) ligand enhances the π-electrophilicity of palladium (II). In this work, we were successful in developing cyclization-carbonylation-cyclization-coupling (CCC-coupling) reaction and an efficient synthetic method of 5-methoxy-3(2H)-furanones utilizing characteristic property of the box-Pd(II) complexes. The former reaction is useful for the synthesis of symmetrical ketones bearing two pharmaceutically important heterocycles, such as indoles, benzofurans, benzothiphenes, and quinolones. In the latter reaction, steroidal compounds bearing spirofuranone structure at C17 were obtained in good yield from alkyne substrates in one-step reactions.
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Report
(4 results)
Research Products
(53 results)
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[Journal Article] Carbonylation of Propargyl Carbamates with Palladium(II) Bisoxazoline Catalysts: Efficient Synthesis of 5-Methyl-3(2H)-furanones2013
Author(s)
Kusakabe, T.; Takahashi, T.; Shen, R.; Ikeda, A.; Dhage, Y. D.; Kanno, Y.; Inouye, Y.; Sasai, H.; Mochida, T.; Kato, K.
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Journal Title
Angew. Chem. Int. Ed.
Volume: 52
Issue: 30
Pages: 7845-7849
DOI
Related Report
Peer Reviewed
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[Presentation] グレガチンBの合成研究
Author(s)
日下部太一, 河合泰子, 加藤恵介
Organizer
第65回有機合成化学協会関東支部シンポジウム
Place of Presentation
新潟薬科大学（新潟県）
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