• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Chemoselective Transformation of C-C Double Bonds by Using Transition-Metal Hediated Electrolysis

Research Project

Project/Area Number 08651011
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionOkayama University

Principal Investigator

KUROBOSHI Manabu  Okayama University, Faculty of Engineering, Lecturer, 工学部, 講師 (30242316)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1997: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsOlefin / Oxidation / Electrolysis / Ruthenium / Osmium / Asymmetric Induction / Natural Product / ジヒドロキシル化 / アミノヒドロキシル化
Research Abstract

In this project were investigated dihydroxylation and aminohydroxylation of carbon-carbon double bonds using transition-metal catalysts.
Chiral diols were obtained from asymmetric electro-dihydroxylation of olefins using osmium and chiral ligands in the presence of a catalytic amount of potassium ferricyanide or iodine. This method was applied to the synthesis of chiral Shikonin. Effects of intramolecular hetero-atom on chiral induction was also studied.
N,N-Dichloro-p-toluenesulfonamide was obtained from electrolysis of p-sulfonamide in aq. NaCl. The dichlorinated sulfonamide was easily hydrolyzed with a basic aqueous solution to give N-chloro-p-toluenesulfonamide. Asymmetric aminohydroxylation of olefins using the chlorinated p-toluenesulfonamide in the presence of chiral osmium catalyst proceeded smoothly to give chiral aminols in moderate yields and ees.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] T.Hase,M.Kuroboshi,T.Katagiri S.Torii,C.Amatore,A.Jutand,H.: "A Facile Synthesis of Biradical Compounds Containing Two N-oxyl Groups Connected with Conjugated π-System" Tetrahedron hett.38. 7391-7394 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Torii,N.Hayashi,M.Kuroboshi: "Electro-Generateed Base Promoted Michael Addition of 4,4-Disubstituted 2,S-Cyclohexαdien1-ous" Synlett. 599-600 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Torii,T.Hase,M.Kuroboshi,T.Katagiri,C.Anatore,A.Jutand,H.Kawafuchi: "Synthesis of Terminal-Biradical Compounds Consisting of Two N.Oxyl Groups Connected with Conjugated π-System" Novel Trends in Electroorganic Sythesis. 87-88 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Jutand,H.Kawafuchi,C.Amatore,M.Kuroboshi,S.Torii: "A Consideration of Mechanism of Tin-Medistool Electron Allylation of Canbonyl Compounds" Novel Treads in Electroorganic Synthesis. 349-350 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kuroboshi,M.Tanaka,S.Kishimoto,H.Tanaka,S.Torii: "Electrochemical Regeneration of Chromium (II).Alkenylation of Carbonyl Compounds" Synlett. 69-70 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Kuroboshi,M.Tanaka,.Kishimoto,K.Goto,H.Tanaka,S.Torii: "Ni/Cr/Al Multi-Metal Rodox-Medisted Alkenylation of Aldehydes" Tetrahedron Lett.in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] HASE Tomoyuki, KUROBOSHI Manabu, KATAGIRI Toshimasa, TORII Sigeru, AMATORE Christian, JUTAND Anny, KAWAFUCHI Hiroyuki: "A Facile Synthesis of Biradical Compounds Containing Two N-Oxyl Groups Connected with Conjugated pi-System" Tetrahedron Lett.38. 7391-7394 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] TORII Sigeru, HAYASHI Naoya, KUROBOSHI Manabu: "Synthesis of 5-Substituted 4,4-Disubstituted 2-Cyclohexen-1-ones by Electro-Generated Base Promoted Michael Addition of 4,4-Disubstituted 2,5-Cyclohexadien-1-ones" Synlett. 599-600 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] TORII Sigeru, HASE Tomoyuki, KUROBOSHI Manabu, KATAGIRI Toshimasa, AMATORE Christian, JUTAND Anny, KAWAFUCHI Hiroyuki: "Synthesis of Terminal-Biradical Compounds Consisting of Two N-Oxyl Groups Connected with Conjugated pi-Systems" Novel Trends in Electroorganic Synthesis (Torii S.Ed) Springer-Verlag Tokyo. 87 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] JUTAND Anny, KAWAFUCHI Hiroyuki, AMATORE Christian, KUROBOSHI Manabu, TORII Sigeru: "A Consideration of Mechanism of Tin-Mediated Electro-Allylation of Carbonyl Compounds" Novel Trends in Electroorganic Synthesis (Torii S.Ed) Springer-Verlag Tokyo. 349 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] KUROBOSHI Manabu, TANAKA Muneaki, KISHIMOTO Suguru, TANAKA Hideo, TORII Sigeru: "Electrochemical Regeneration of Chromium (II).Alkenylation of Carbonyl Compounds" Synlett. 69-70 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] KUROBOSHI Manabu, TANAKA Muneaki, KISHIMOTO Suguru, GOTO Kentaro, TANAKA Hideo, TORII Sigeru: "Ni/Cr/Al Multi-Metal Redox-Mediated Alkenylation of Aldehydes" Tetrahedron Lett.(in Press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] S.Torii, T.Hase, M.Kuroboshi, C.Amatore, A.Jutanal, H.Kawafuchi: "Synthesis of Terminal-Biradical Compounds Consisting of Two N-Oxyl Groups Connected with Conjugated π-Systems" Tetrahedron Letters. 38(42). 7391-7394 (1997)

    • Related Report
      1997 Annual Research Report

URL: 

Published: 1996-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi