Development of Bronsted Acid-Metal Bifunctional Catalyst Based on Bisamidine Framework
| Project/Area Number |
20750082
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Rikkyo University |
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Principal Investigator |
YAMANAKA Masahiro Rikkyo University, 理学部, 准教授 (60343167)
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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 |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | 触媒的不斉合成 / 触媒設計 / ビスアミジン配位子 / 亜鉛ビスアミジナート / ルイスーブレンステッド複合酸 / 不斉アルキル化反応 / 不斉向山アルドール反応 / 不斉Friedel-Crafts反応 / 金属触媒 / 有機分子触媒 / 二核亜鉛ビスアミジナート / ルイス-ブレンステッド複合酸 / 不斉ヒドロホスホニル化反応 / 不斉ヒドロボスホニル化反応 / 二核金属触媒 / 向山アルドール反応 / ルイスーブレンステッド複合酸触媒 / 二核亜鉛アミジナート / 銅-ビスアミジン |
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| Research Abstract |
The rational design and development of a highly efficient catalyst for asymmetric catalytic reaction is of ongoing considerable interest in organic chemistry. Focusing on the steric and electronic properties of the bisamidine framework, two types of chiral catalysts were developed. The cationic zinc bisamidine complex acts as a Bronsted-Lewis combined acid to promote asymmetric Mukaiyama aldol reaction of α-ketoesters. The aldol products were obtained in good yields but with low enantioselectivities. Addition of the fluoroalcohol having suitable acidity and bulkiness led to dramatic increase in enatioselectivity. The multinuclear zinc bisamidinate catalyzed asymmetric alkylation of α-ketoesters to afford the products in high yields and enantioselectivities.
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Report
(4 results)
Research Products
(38 results)
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[Journal Article] Chiral Phosphoric Acid Catalyzed Desymmetrization of meso-1,3-Diones : Asymmetric Synthesis of Chiral Cyclohexenones2009
Author(s)
Mori, K., Katoh, T., Suzuki, T., Noji, T., Yamanaka, M., Akiyama, T
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Journal Title
Angewandte.Chemistry Int.Ed. 48
Pages: 9652-9654
Related Report
Peer Reviewed
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[Journal Article] Chiral Bronsted Acid Catalyzed Hydrophosphonylation of Imines-DFT Study on the Effect of Substituents of Phosphoric Acid2009
Author(s)
Akiyama, T., Morita, H., Bachu, P., Mori, K., Yamanaka, M., Hirata, T.
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Journal Title
Tetrahedron 65
Pages: 4950-4956
Related Report
Peer Reviewed
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