1998 Fiscal Year Final Research Report Summary
Selective Electrosynthesis of Biologically Active Organofluorine Compound Using a Fluorine Mediator
| Project/Area Number |
09650949
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | TOKYO INSTITUTE OF TECHNOLOGY |
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Principal Investigator |
FUCHIGAMI Toshio Tokyo Institute of Technology, Interdisciplinary Graduate School of Sciences and Engineering Professor, 大学院・総合理工学研究科, 教授 (10016701)
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| Project Period (FY) |
1997 – 1998
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| Keywords | Stereoselective synthesis / Mediator / Biologically active compound / Anodic substitution / Anodic cycliation / Organofluorine compound / Oxathiolane / Chiral compound |
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| Research Abstract |
Although anodic substitutions are quite useful in organic synthesis since they can be done in one step, such subsitutions are limited to organic nitrogen compounds. Recently, we found that fluoride ions markedly promoted anodic substitutions of chalcogeno compounds. On the other hand, development of efficient selective synthetic methods of organofluorine compounds has been increasingly important since they have unique biological activities. However, due to specific fluorine atoms, their synthesis is not always easy.
From these viewpoints, we have attempted selective electrosynthesis of biologically active organofluorine compounds using a fluorine mediator as follows.
1) Fluoride ion mediated anodic alpha-methoxylation of 2-methoxy-3,3,3-trifluoropropyl phenyl sulfide and its synthetic application.
2) Electrosynthesis of beta-trifluoromethylated O,S-acetal and alpha-(trifluoromethyl)acrylate derivatives from 2-ethoxycarbonyl-3,3,3-trifluoropropyl phenyl sulfide using a fluoride ion mediator.
3) Fluoride ion mediated anodic alpha-methoxylation of 2-hydroxy-3,3,3-trifluoropropyl phenyl sulfide and its application to the synthesis of optically active organofluorine compounds.
4) Electrosynthesis of optically active oxathiolanes having a CF_3 group using a fluoride ion mediator.
We have acieved above four projects and found that some of electrosynthsized products show maked biological activities.
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