| Project/Area Number |
16K13993
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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 |
Synthetic chemistry
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| Research Institution | Toyohashi University of Technology |
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Principal Investigator |
Shibatomi Kazutaka 豊橋技術科学大学, 工学(系)研究科(研究院), 准教授 (00378259)
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| Project Period (FY) |
2016-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | 脱炭酸反応 / 不斉合成 / 有機分子触媒 / 塩素化反応 / ハロゲン化反応 / SN2反応 / カルボン酸 / 脱炭酸 / キラルアミン触媒 / 不斉ハロゲン化反応 / 触媒的不斉合成 / 合成化学 / ハロゲン化合物 / キラル触媒 / 医薬品合成 |
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| Outline of Final Research Achievements |
Although decarboxylative halogenation of aliphatic carboxylic acids is known to be a useful synthetic method for the preparation of a variety of organohalides, an enantioselective version of this reaction has not been reported so far. In this research, we succeeded in developing a highly enantioselective decarboxylative chlorination of b-ketocarboxylic acids to yield a-chloroketones. The reaction proceeded with high enantioselectivity (up to 98% ee) in the presence of chiral primary amine catalyst. The resulting a-chloroketones could be converted into a-aminoketones and a-thio-substituted ketones via SN2 reactions. Our results offer the first example of enantioselective decarboxylative halogenation of carboxylic acids.
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