2018 Fiscal Year Final Research Report
Development of Advanced Molecular Transformation Methods Catalyzed by Chiral Silver Alkoxides
| Project/Area Number |
16K05766
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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 |
Synthetic chemistry
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| Research Institution | Chiba University |
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Principal Investigator |
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Keywords | 有機化学 / 触媒・化学プロセス / 不斉反応 / エノラート / キラル触媒 |
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| Outline of Final Research Achievements |
We have examined methods for efficiently generating chiral silver(I) methoxide with high purity as well as methods for preparing chiral silver(I) enolates from the methoxide. As a result, we have found that the Hunig base or triethylamine is effective as an additive for the purpose and desired chiral silver(I) methoxide and the corresponding chiral silver(I) enolates can be prepared with high purities. When asymmetric aldol reaction of isatin derivatives via a chiral silver(I) enolate has been performed using this method, a high level of asymmetric induction has been observed for the aldol products. Asymmetric nitrosoaldol reaction, asymmetric allylation of aldehydes, and asymmetric allenylation/propargylation of aldehydes have been also attained by applying the present catalytic method of generating chiral silver(I) enolates to various electrophiles.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
本研究課題はこれまでほとんど知見の無かった銀(I)アルコキシドを効率的に発生させ、様々な有機合成反応への応用をねらったものである。本研究によってキラル銀(I)アルコキシドが純度良く調製でき、その性質が明らかにされた事、さらにはキラル銀(I)アルコキシドによって発生させたキラル銀エノラートの反応が、他の金属エノラートと異なる反応性、選択性を示せた事は学術的観点から意義のある成果であると考えられる。さらに研究期間内に開発した位置・立体選択的反応が、従来法では合成困難な有用化合物、中でも生理活性化合物の効率的合成手法として応用されれば、医農薬の分野にも貢献できる社会的意義のある成果となる。
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