Development of C2-Symmetric Pyridine N-Oxides as New Nucleophilic Catalysts and Application for the Asymmetric Synthesis
| Project/Area Number |
23655045
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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 |
Organic chemistry
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| Research Institution | Tokyo University of Science |
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Principal Investigator |
SHIINA Isamu 東京理科大学, 理学部, 教授 (40246690)
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| Project Period (FY) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
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| Keywords | 有機化学 / 有機合成化学 / 不斉触媒 / 求核性塩基触媒 / 不斉合成 / 光学分割 / 求核性塩基 / 軸不斉 / 不斉配位子 |
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| Research Abstract |
We had found an effective coupling reaction of carboxylic acids and alcohols using aromatic anhydrides by the promotion of nucleophilic base catalysts, such as DMAP and DMAPO. Furthermore, we have developed a method for the preparation of optically active carboxylic esters by the kinetic resolution of racemic secondly alcohols using carboxylic anhydrides, and achiral carboxylic acids via mixed-anhydride formation method in the presence of chiral acyl-transfer catalysts. In this study, we succeeded in preparing new pyridine oxide compounds (DM-DMAPO and DM-DMQO) and other nucleophilic base catalysts. Moreover, the following reactions were performed in the presence of any of these as a catalyst, (1) a process for producing an ester or amide compound from a carboxylic acid equivalent and an alcohol or amine, (2) an asymmetric esterification reaction, and (3) an asymmetric aldol and allylation reactions.
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Report
(4 results)
Research Products
(54 results)
