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Development of Novel Asymmetric Fluorination Using Electrolysis

Research Project

Project/Area Number 11650885
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

FUCHIGAMI Toshio  Tokyo Institute of Technology, Interdisciplinary Graduate School of Science and Engineering Professor, 大学院・総合理工学研究科, 教授 (10016701)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2000: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1999: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsAsymmetric Fluorination / Anodic Fluorination / Trifluorinated Sulfide / Thiazolidine / Selective Fluorination / Chiral Auxiliary / Chiral Fluoroorganics / Diastereoselective Fluorination / 電解不斉フッ素化 / 分子内不斉誘導 / ジアステレオ選択性 / α-フェニルチオ酢酸エステル / 超音波電解 / 電解フッ素化 / モノフルオロ化合物 / スルフィド / 1,3-チアゾリジン / L-システイン / 隣接基関与 / 1,2-不斉誘導
Research Abstract

Chiral organofluorine compounds are highly useful for medicines, agrochemicals, and functional materials. Optical resolution, biological and chiral fluorobuilding block methods have been mainly employed so far. Asymmetric fluorination seems to be the mostideal method for the preparation of chiral organofluorine compounds. However, studies on asymmetric fluorination have been limited and there have been few successful examples.
On the other hand, we have recently developed versatile selective anodic fluorination of organic compounds.
With these in mind, asymmetric anodic fluorination using various chiral induction methods has been attempted as follows :
1) Diastereoselective Anodic Fluorination of Thiazolidines
2) Highly Diastereoselective Anodic Fluorination of 3, 3, 3-Trifluoro-2-methoxypropyl Sulfides
3) Diastereoselective Anodic Fluorination of a-Phenylthioacetates Having Chiral Auxiliaries
We have achieved above three projects and the results obtained in these projects would be highly useful for further studies on asymmetric anodic fluorination of various organic molecules.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] 渕上寿雄: "Organic Electrochemistry. 4th Ed."Marcel Dekker. 52 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 渕上寿雄: "フッ素系生理活性物質の進歩と応用展開-電解フッ素化法"シーエムシー. 15 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Fuchigami: ""Electrochemical Fluorination Method" in "Development of Fluorinated Biologically Active Compounds" ed. T.Taguchi"CMC, Tokyo. 54-68 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Nonaka and T.Fuchigami: ""Stereochemistry of Organic Electrode Processes" in "Organic Electrochemistry. 4th ed." ed. H.Lund and O.Hammerich"Marcel Dekker, NY. 1051-1102 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S'ayed M.Riyad: "Highly Regioselective Anodic Mono-and Difluorination of Propargyl Sulfides and Preparation of α-Fluoroallenyl Sulfides"Tetrahedron Letters. 42.(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 淵上寿雄: "Organic Electrochemistry,4th Ed."Dekker. 17 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 淵上寿雄: "最新電極触媒の科学"北海道大学図書刊行会. 15 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kamal M.Dawood: "Anodic Fluorination of 2-Pyrimidyl,2-Pyridyl,and 2-Quinazolinonyl Sulfides"Journal of Organic Chemistry. 64・21. 7935-7939 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 渕上寿雄: "Advances in Electron Transfer chemistry.Vol.6."JAI Press. 99 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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