Synthesis of enzyme mimic dual activation catalyst and its application for asymmetric synthesis
| Project/Area Number |
17550098
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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 |
YAMAMOTO Iwao Shinshu Univ., Functional Polymer Science, Assoc. Prof., 繊維学部, 教授 (60021169)
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| Co-Investigator(Kenkyū-buntansha) |
FUJIMOTO Tetsuya Shinshu Univ., Functional Polymer Science, Assoc. Prof, 繊維学部, 助教授 (90209099)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2006: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2005: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | asymmetric synthesis / synthetic enzyme / dual activation catalyst / bisoxazoline / 不斉シアノアリル化反応 / 不斉シアノシリル化反応 |
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| Research Abstract |
The asymmetric allylation reactions of aldehydes catalyzed by a 10 mol% bisoxazoline complex bearing a phosphine oxide moiety(PM-Box), which was newly designed and synthesized from L-serine, afforded the corresponding homoallylic alcohols in 48-74% yields with 39-86% ee. The reaction proceeds with the dual activation of the aldehyde and allylsilane by the Lewis acid and base of the catalyst. The evidence for the activation of the allylsilane was clarified by the ^<31>P NMR spectra.
The PM-Box-Cu(OTf)2 complex worked effectively in asymmetric reaction of imines with trimethylsilylsilane. For example, a reaction of benzylidene-N-benzhydrilimene with trimethylsilylsilane in the presence of 3mol% of PM-Box-Cu(OTf)2 gave a corresponding homoallyl amine in 91% yield with 90%ee. Furthermore, Strecker reactions of ketimines in the presence of 3mol% of the catalyst afford the product up to 96%ee.
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Report
(3 results)
Research Products
(3 results)
