2023 Fiscal Year Final Research Report
Development of Highly Difficult Asymmetric Fluorinations with Anionic Phase-Transfer Catalyst
| Project/Area Number |
21K06479
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | University of Shizuoka |
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Principal Investigator |
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| Project Period (FY) |
2021-04-01 – 2024-03-31
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| Keywords | フッ素 / 触媒 / 不斉 |
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| Outline of Final Research Achievements |
Although we tried to investigate the asymmetric C-H fluorination with a chiral dicarboxylate phase-transfer catalyst, which was developed by our group and was expected to extend its functionality to have multiple roles as the chiral counter anion of Pd catalyst and as a base unit during C-H activation, our dicarboxylate did not promote the C-H fluorination. Therefore, we designed a new multifunctional chiral carboxylic acid for the C-H fluorination and established its synthetic method. The C-H fluorination was found to proceed under Pd-catalysis with the chiral carboxylic acid.
On the other hand, we have successfully developed the asymmetric fluorocyclization of difluoroalkenes under anionic phase-transfer conditions, where fluorofunctionalizations of electron deficient alkenes are still difficult. To our best knowledge, this is the first report on the asymmetric fluorocyclization of difluoroalkenes.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
新しいフッ素化合物を供給する方法論の開発は、生命科学研究において重要な継続課題である。しかしながら、最も効率的と考えられるC-H結合のフッ素化に関して、その立体制御を成す一般的な方法論は未だ確立されていない。そのため、C-Hフッ素化反応の立体制御法の開発を目指した本研究は学術的な意義および挑戦性が高い。
本研究で蓄積した知見から、C-Hフッ素化反応のための新たなキラルカルボン酸の基礎デザインを構築することに成功した。今後より洗練された触媒系に昇華することで、キラルフッ素化合物のケミカルスペースが拡充されることが期待できる。
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