2018 Fiscal Year Research-status Report
Synthesis of Lactones and Amino Acids via Reductive Carboxylation Reactions
| Project/Area Number |
18K05099
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| Research Institution | The University of Tokyo |
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Principal Investigator |
ユー ウージン 東京大学, 大学院理学系研究科(理学部), 特任講師 (70626077)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Keywords | carbon dioxide / mutli-component coupling / lactone / lactam / fluorine |
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| Outline of Annual Research Achievements |
Our research goal is to develop new multi-component coupling reactions with carbon dioxide to prepare complex organic compounds. We have found that propargyl alcohols can undergo a sequential trans-hydrometallation reaction, and these intermediates can be utilized as substrates for catalytic carboxylation reactions, using copper or silver salts as catalysts, to furnish various lactones. The corresponding propargyl amines were also shown to undergo similar transformations to generate lactams. We also developed a fluorocarboxylation reaction of gem-difluoroalkenes using cesium fluoride and carbon dioxide as coupling partners. We found that this multi-component reaction can be achieved without any additives or catalysts, and various trifluoromethyl carboxylic acids could be obtain in good yields.
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| Current Status of Research Progress |
Current Status of Research Progress
1: Research has progressed more than it was originally planned.
Reason
We were able to get positive results earlier than expected and one project has been published and another project is in the advance stages of completion.
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| Strategy for Future Research Activity |
The future plan is to continue our investigations into developing multi-component carboxylation reactions. We will finish up our project for the synthesis of lactones and lactams using propargyl alcohols and amines as substrates. In particular, we will focus on using this synthetic methodology to prepare biologically active natural products. Once this project is completed, then we will continue to investigate the general strategy of combining efficient metallation with catalytic carboxylation reactions to prepare complex carboxylic acids and its derivatives. We will also focus our efforts to develop fluorine-based carboxylic acids using gem-difluoroalkenes and carbon dioxide as substrates, and our current focus is on the synthesis fluorinated amino acids.
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Research Products
(4 results)
