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Study on the Preparation of Novel and Chiral Organohypervalent Iodine Compounds and Their Use for Chiral Oxidation

Research Project

Project/Area Number 10640511
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

TOGO Hideo  Chiba University Department of Chemistry Faculty of Science Associate Professor, 理学部, 助教授 (60217461)

Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2000: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1998: ¥2,100,000 (Direct Cost: ¥2,100,000)
KeywordsChiral Oxidation / Sulfoxide / Hypervalent Iodine Compounds / Axial Chirality / 不斉炭素 / 不斉有機超原子価ヨウ素化合物 / 酸化反応 / 不斉酸化反応 / 分子内不斉配位子
Research Abstract

Based on the high reactivity of organo-hypervalent iodine compounds for functional group conversion, the target of the present study is that the preparation of novel chiral trivalent iodine compounds ; type A : bearing a chiral alkoxy ligand on the iodine atom, type B : axial chirality on the iodine atom, and their synthetic use for the chiral oxidation of substrates.
At the first year, the preparation of novel iodoarenes bearing a chiral center of alkoxy group at the ο-position, and the conversion to the corresponding cyclic trivalent iodine form (type A) were carried out, and the reactivity for the oxidation of sulfides were studied. At the second year, the preparation of organo-trivalent iodine compounds bearing an axial chiral center at the iodine atom (type B) were carried out. All these new compounds were characterized by ^1H-NMR, ^<13>C-NMR, and finally X-ray crystal analysis of the compounds. At the last year, the preparation of chiral trivalent iodine compounds bearing an alkoxy ligand (type A) was established via the oxidation of the chiral iodoarenes, and the chiral oxidation of sulfides was carried out to give the corresponding sulfoxides in good yields with moderate e. e. Actually, the present results are not enough for the practical use of chiral oxidation with the present chiral organo-trivalent iodine compounds. However, it is useful results for the design of good chiral organo-hypervalent iodine compounds for oxidation.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (58 results)

All Other

All Publications (58 results)

  • [Publications] H.Togo,Y.Hoshina,T.Muraki,H.Nakayama,and M.Yokoyama: "Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo) arenes"Journal of Organic Chemistry. 63. 5193-5200 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,W.He,Y.Waki,M.Yokoyama,: "C-Glycosidation Technology with Free Radical Reactions"Synlett. 700-717 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,G.Nogami,and M.Yokoyama,: "Synthetic Application of Poly [styrene (iodoso diacetate)]"Synlett. 534-536 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,M.Katohgi,and M.Yokoyama,: "Direct Preparation of Saccharin Skeletons from N-Methyl (o-methyl) arenesulfonamides with (Diacetoxyiodo) arenes"Synlett. 131-132 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki,H.Togo,and M.Yokoyama,: "Synthetic Use of 1-(p-Toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one : Iodination of Aromatic Rings"Synlett. 286-288 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki,H.Togo,S.Matsubayashi: "1,1,2,2-Tetraphenyldisilane as a Diversified Radical Reagent"Tetrahesron Letters. 39. 1921-1924 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki,H.Togo,and M.Yokoyama,: "Reactivity in the Formation of Lactones from Aromatic Carboxylic Acids with Organohypervalent Iodine Compounds in the Suarez System"Journal of Chemical Society, Perkin Transaction 1. 63. 1713-1716 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki,H.Togo,S.Matsubayashi: "Tetraaryldisilanes as a Novel Strategic Radical Reagent"Tetrahedron. 55. 3735-3747 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki,H.Togo,and M.Yokoyama,: "Reactivity and Synthetic Utility of 1-(Arenesulfonyloxy) benziodoxolones"Journal of Organic Chemistry. 64. 2883-2889 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki,H.Togo,and M.Yokoyama,: "Synthetic Utility of 1,1,2,2-Tetraaryldisilanes : Radical Reduction of Alkyl Phenyl Chalcogenides"Journal of Chemical Society, Perkin Transaction 1. 2891-2896 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,S.Abe,G.Nogami,and M.Yokoyama,: "Synthetic Use of Poly [4-(diacetoxyiodo) styrene] for Organic Reactions"Bulletin of Chemical Society of Japan. 72. 2351-2356 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Katohgi,H.Togo,K.Yamaguchi,and M.Yokoyama,: "New Synthetic Method to 1,2-Benzisothiazoline-3-one-1,1-dioxides and 1,2-Benzisothiazoline-3-one-1-oxides from N-Alkyl (o-methyl) arenesulfonamides"Tetrahedron. 55. 14885-14900 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,Y.Harada,and M.Yokoyama,: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide Skeleton from N-Methyl 2-(Aryl) ethanesulfonamides with (Diacetoxyiodo) arenes"Journal of Organic Chemistry. 65. 926-929 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,S.Matsubayashi,O.Yamazaki,and M.Yokoyama,: "Deoxygenative Functionalization of Hydroxy Groups via Xanthates with Tetraphenyldisilane"Journal of Organic Chemistry. 65. 2816-2819 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki,M.Yokoyama,and H.Togo,: "Iodophosphoryloxylation of Carbon-Carbon Multi-Bonds and Its Application to Glycals"Journal of Organic Chemistry. 65. 4679-4684 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki,K.Yamaguchi,M.Yokoyama,and H.Togo,: "Radical Cyclization of O-Glycosides Using 1,1,2,2-Tetraphenyldisilane as a Radical Reagent : Preparation of Bicyclic Sugars"Journal of Organic Chemistry. 65. 5440-5442 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Katohgi,M.Yokoyama,and H.Togo: "Novel Sonochemical Dealkylation of N-Alkylsulfonamides in the Presence of (Diacetoxyiodo) benzene and Iodine"Synlett. 1055-1057 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,T.Nabana,and K.Yamaguchi,: "Preparation and Reactivities of Novel (Diacetoxyiodo) arenes Bearing Heteroaromatics"Journal of Organic Chemistry. 65. 8391-8394 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 東郷秀雄: "有機フリーラジカルの化学"講談社サイエンティフック. 190 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, Y.Hoshina, T.Muraki, H.Nakayama, and M.Yokoyama: "Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo) arenes"J.Org.Chem.. 63. 5193-5200 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, W.He, Y.Waki, M.Yokoyama: "C-Glycosidation Technology with Free Radical Reactions"Synlett. 700-717 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, G.Nogami, and M.Yokoyama: "Synthetic Application of Poly [styrene (iodoso diacetate)]"Synlett. 534-536 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, M.Katohgi, and M.Yokoyama: "Direct Preparation of Saccharin Skeletons from N-Methyl (ο-methyl) arenesulfonamides with (Diacetoxyiodo) arenes"Synlett. 131-132 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki, H.Togo, and M.Yokoyama: "Synthetic Use of 1-(p-Toluenesulfonyloxy)-1, 2-benziodoxol-3(1H)-one : Iodination of Aromatic Rings"Synlett. 286-288 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] W.He, H.Togo, Y.Waki, and M.Yokoyama: "Application of the Versatile Character of the Tellurium Atom for the Synthesis of C-Nucleoside Analogues via Sugar Tellurides"J.Chem.Soc., Perkin Trans 1. 2425-2433 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki, H.Togo, S.Matsubayashi, and M.Yokoyama: "1, 1, 2, 2-Tetraphenyldisilane as a Diversified Radical Reagent"Tetrahesron Lett. 39. 1921-1924 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki, H.Togo, S.Matsubayashi, and M.Yokoyama: "Tetraaryldisilanes as a Novel Strategic Radical Reagent"Tetrahedron. 55. 3735-3747 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki, H.Togo, and M.Yokoyama: "Reactivity and Synthetic Utility of 1-(Arenesulfonyloxy)-benziodoxolones"J.Org.Chem.. 64. 2882-2889 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki, H.Togo, and M.Yokoyama: "Reactivity in the Formation of Lactones from Aromatic Carboxylic Acids with Organohypervalent Iodine Compounds in in the Suarez System"J.Chem.Soc., Perkin Trans 1. 1713-1716 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki, H.Togo, and M.Yokoyama: "Synthetic Utility of 1, 1, 2, 2-Tetraaryldisilanes : Radical Reduction of Alkyl Phenyl Chalcogenides"J.Chem.Soc., Perkin Trans.1. 2891-2896 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, S.Abe, G.Nogami, and M.Yokoyama: "Synthetic Use of Poly [4-(diacetoxyiodo) styrene] for Organic Reactions"Bull.Chem.Soc.Jpn.. 72. 2351-2356 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Katohgi, H.Togo, K.Yamaguchi, and M.Yokoyama: "New Synthetic Method to 1, 2-Benzisothiazoline-3-one-1, 1-dioxides and 1, 2-Benzisothiazoline-3-one-1-oxides from N-Alkyl (ο-methyl) arenesulfonamides"Tetrahedron. 55. 14885-14900 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, Y.Harada, and M.Yokoyama: "Preparation of 3,4-Dihydro-2, 1-benzothiazine 2, 2-Dioxide Skeleton from N-Methyl 2-(Aryl) ethanesulfonamides with (Diacetoxyiodo)-arenes"J.Org.Chem.. 65. 926-929 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, S.Matsubayashi, O.Yamazaki, and M.Yokoyama: "Deoxygenative Functionalization of Hydroxy Groups via Xanthates with Tetraphenyldisilane"J.Org.Chem.. 65. 2816-2819 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Muraki, M.Yokoyama, and H.Togo: "Iodophosphoryloxylation of Carbon-Carbon Multi-Bonds and Its Application to Glycals"J.Org.Chem.. 65. 4679-4684 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] O.Yamazaki, K.Yamaguchi, M.Yokoyama, and H.Togo: "Radical Cyclization of ο-Glycosides Using 1, 1, 2, 2-Tetrapheny-disilane as a Radical Reagent : Preparation of Bicyclic Sugars"J.Org.Chem.. 65. 5440-5442 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Katohgi, M.Yokoyama, and H.Togo: "Novel Sonochemical Dealkylation of N-Alkylsulfonamides in the Presence of (Diacetoxyiodo) benzene and Iodine"Synlett. 1055-1057 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo, T.Nabana, and K.Yamaguchi: "Preparation and Reactivities of Novel (Diacetoxyiodo) arenes Bearing Heteroaromatics"J.Org.Chem.. 65. 8391-8394 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Togo,Y.Harada,and M.Yokoyama,: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide Skeleton from N-Methyl 2-(Aryl) ethanesulfonamides with (Diacetoxyiodo) arenes"Journal of Organic Chemistry. 65. 926-929 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.Togo,S.Matsubayashi,O.Yamazaki,and M.Yokoyama,: "Deoxygenative Functionalization of Hydroxy Groups via Xanthates with Tetraphenyldisilane"Journal of Organic Chemistry. 65. 2816-2819 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Muraki,M.Yokoyama,and H.Togo,: "Iodophosphoryloxylation of Carbon-Carbon Multi-Bonds and Its Application to Glycals"Journal of Organic Chemistry. 65. 4679-4684 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] O.Yamazaki,K.Yamaguchi,M.Yokoyama,and H.Togo,: "Radical Cyclization of 0-Glycosides Using 1,1,2,2-Tetraphenyldisilane as a Radical Reagent : Preparation of Bicyclic Sugars"Journal of Organic Chemistry. 65. 5440-5442 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Katohgi,M.Yokoyama,and H.Togo: "Novel Sonochemical Dealkylation of N-Alkylsulfonamides in the Presence of (Diacetoxyiodo) benzene and Iodine"Synlett,. 1055-1057 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.Togo,T.Nabana,and K.Yamaguchi,: "Preparation and Reactivities of Novel (Diacetoxyiodo) arenes Bearing Heteroaromatics"Journal of Organic Chemistry. 65. 8391-8394 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 東郷秀雄: "有機フリーラジカルの化学"講談社サイエンティフック. 190 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] O. Yamazaki, H. Togo, S. Matsubayashi: "Tetraaryldisilanes as a Novel Strategic Radical Reagent"Tetrahedron. 55. 3735-3747

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Muraki, H. Togo and M. Yokoyama: "Reactivity and Synthetic Utility of 1-(Arenesulfonyloxy)- benziodoxolones"The Journal of Organic Chemistry. 64. 2883-2889 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Muraki, H. Togo and M. Yokoyama: "Reactivity in the Formation of Lactones from Aromatic Carboxylic Acids with Organohypervalent Iodine Compounds in the Suarez System"Journal of the Chemical Socity, Perkin Trans. 1. 1713-1716 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] O. Yamazaki, H. Togo, M. Yokoyama: "Synthetic Utility of 1,1,2,2-Tetraaryldisilanes: Radical Reduction of Alkyl Phenyl Chalcogenides"Journal of the Chemical Socity, Perkin Trans. 1. 2891-2896 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H. Togo, S. Abe, G. Nogami and M. Yokoyama: "Synthetic Use of Poly[4-(diacetoxyiodo)styrene] for Organic Reactions"Bulletin of the Chemical Society of Japan. 72. 2351-2356 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M. Katohgi, H. Togo, K. Yamaguchi: "New Synthetic Method to 1,2-Benzisothiazoline-3-one-1,1-dioxides and 1,2-Benzisothiazoline-3-one-1-oxides from N-Alkyl(o-methyl)arenesulfonamides"Tetrahedron. 55. 14885-14900 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H. Togo,Y. Hoshina,T. Muraki,H. Nakayama: "Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo) arenes" Journal of Organic Chemistry. 63. 5193-5200 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H. Togo,W. He,Y. Waki,M. Yokoyama: "C-Glycosidation Technology with Free Radical Reactions" Synlett. 700-717 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H. Togo,G. Nogami,and M. Yokoyama: "Synthetic Application of Poly[styrene(iodoso diacetate)]" Synlett. 534-536 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H. Togo,M. Katohgi,and M. Yokoyama: "Direct Preparation of Saccharin Skeletons from N-Methyl(0-methyl)arenesulfonamides with(Diacetoxyiodo)arenes" Synlett. 131-132 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T. Muraki,H. Togo,and M. Yokoyama: "Synthetic Use of 1-(p-Toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one:Iodination of Aromatic Rings" Synlett. 286-288 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] W. He,H. Togo,Y. Waki,and M. Yokoyama: "Application of the Versatile Character of the Tellurium Atom for the Synthesis of C-Nucleoside Analogues via Sugar Tellurides" Journal of the Chemical Society,Perkin Trans 1. 2425-2433 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S. Murahashi編集: "Reactive Organometallics" Kodansha, 530 (1998)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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