2002 Fiscal Year Final Research Report Summary
Superacid-catalyzed reactions and the application of supercritical fluid
| Project/Area Number |
13554023
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Organic chemistry
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| Research Institution | The University of Tokyo |
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Principal Investigator |
OHWADA Tomohiko Graduate School of Pharmaceutical Sciences, The University of Tokyo, Professor, 大学院・薬学系研究科, 教授 (20177025)
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| Project Period (FY) |
2001 – 2002
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| Keywords | superacids / aromatic compounds / Pictet-Spengler reaction / CO2 supercritical fluid / stereoselction / Superelectrophile / intramolecular cyclization / nitroalkanes |
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| Research Abstract |
New superacid-catalyed reactions and their features such as regioselectivity and stereoseterctivity were studied. Destabilized carbenium ions substituted with genuine electron-withdrawing groups such as carbenium, oxonium, ammonium groups were proposed to be involved. These cations constitute reactive superelectrophiles in a novel type of Friedel-Crafts reactions. We attempted to use CO_2 supercritical fluid conditions with a combination of superacid catalyst. We understood the development of new reaction system compatible with the superacid. We studied (1) Regioselective Superacid-Catalyzed Electrocyclization of Diphenylmethyl Cations. Fluorenes, Phenanthrol and Benzofuran Cyclizations (2) Stereoselectivity of Superacid-Catalyzed Pictet-Spengler Cyclization Reactions (3) 4H-l,2-Benzoxazines with Electron-withdrawing Substituents on the Benzene Ring. Synthesis and Application as Potent Intermediates for Oxygen-Functionalized Aromatic Compounds
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