Development of wide scope asymmetric synthesis of oxygen-bridged polycyclic compounds and its synthetic applications
| Project/Area Number |
20550094
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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 |
Synthetic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
SUGA Hiroyuki Shinshu University, 工学部, 教授 (60211299)
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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 |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | 選択的合成・反応 / 錯体・有機金属触媒 / 不斉合成・反応 / 触媒設計・反応 / 1,3-双極子 / 付加環化 / カルボニルイリド / 不斉合成 / ジアゾ化合物 / キラルルイス酸 / エナンチオ選択性 / 生理活性 |
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| Research Abstract |
Lewis acid catalyzed asymmetric cycloaddition reactions of cyclic carbonyl ylides generated from diazo carbonyl compounds were found to proceed not only by a normal electron demand type but also by an inverse electron demand type such as in the reaction with vinyl ethers and N-methylindoles with high levels of asymmetric induction. Thus a wide scope procedure for asymmetric syntheses of oxygen-bridged polycyclic compounds has been developed. With regard to a generality of diazo carbonyl substrates, the procedure could be applied for not only diazo compounds containing a benzene ring but also acyclic diazo diketones and the substrates containing a pyrrolidine ring. For the synthetic application, the synthesis of (+)-Tashiromine has been achieved.
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Report
(4 results)
Research Products
(29 results)
