2022 Fiscal Year Final Research Report
asymmetric photocyclization reaction controlled by ammonium-pi interaction
Project/Area Number |
20K05490
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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Research Institution | Ochanomizu University |
Principal Investigator |
YAMADA Shinji お茶の水女子大学, 基幹研究院, 教授 (30183122)
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Project Period (FY) |
2020-04-01 – 2023-03-31
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Keywords | 選択的合成 / カチオンーπ相互作用 / 光化学反応 |
Outline of Final Research Achievements |
In this research project, we have investigated the interaction of iminium or tetraalkylammonium with the π-plane in the following two photoreactions: (1) [2+2] photodimerization of conjugated iminium salts, and (2) Norrish-Yang reaction of oxazolidinones in the presence of ammonium salts. As a result, we found that the stereochemistry in the adducts and cyclization products that could not be obtained by conventional methods were obtained with high selectivity. These results were attributed to the control of the crystal arrangement by the iminium-π interaction and the control of the transition state of the reaction by the interaction between ammonium and the substrate.
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Free Research Field |
複合化学
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Academic Significance and Societal Importance of the Research Achievements |
カチオンーπ相互作用は、カチオンとπ面との相互作用であり1,2)、近年、有機合成分野において本相互作用の利用が注目を集めている3)。本研究では、分子間イミニウム-π相互作用、および基質とテトラアルキルアンモニウムとのカチオン-π相互作用により、従来困難であった生成物の立体化学を制御することができた。これにより、カチオン-π相互作用の有機合成化学への更なる有用性を示すことができた。
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