Innovative Organocatalysis in Cooperation with Wood Nanocellulose and Amino Acids
| Project/Area Number |
26660145
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Wood science
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| Research Institution | Kyushu University |
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Principal Investigator |
KITAOKA Takuya 九州大学, (連合)農学研究科(研究院), 教授 (90304766)
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | ナノセルロース / プロリン / 有機分子触媒 / アルドール反応 / カルボキシ基 / マトリックス効果 / 不斉合成 / 界面反応 / 立体制御 / アルドール縮合 |
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| Outline of Final Research Achievements |
Catalysts accelerate various chemical reactions with high selectivity. In recent, “organocatalysts” have attracted much attention in chemistry, instead of rare metals and enzymes. Proline is well known as a first organocatalyst to catalyze an asymmetric aldol reaction; however it involves many difficulties in practical applications. Herein, we propose the interfacial aldol synthesis by the combination of proline and TEMPO-oxidized cellulose nanofibers. The aldol reaction of 4-nitrobenzaldehyde and acetone proceeded stoichiometrically and enantioselectively to synthesize (4R)-4-hydroxy-4-(4-nitrophenyl)-2-butanone. Proline alone showed very low catalytic efficiency and provided only racemic products. Thus, the cooperative interactions of catalysts and substrates on the crystalline nanocellulose must be a critical factor to enhance such asymmetric aldol reaction. Our challenge in pairing nanocellulose with organocatalysts will provide a new insight to interfacial asymmetric synthesis.
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Report
(3 results)
Research Products
(25 results)
