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Development of New Synthetic Reactions Using High Efficient Acidic Catalysts

Research Project

Project/Area Number 04453029
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionScience University of Tokyo

Principal Investigator

MUKAIYAMA Teruaki  Science Univ.of Tokyo Professor, 理学部, 教授 (60016003)

Co-Investigator(Kenkyū-buntansha) 小林 修  東京理科大学, 理学部, 助教授 (50195781)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥7,200,000 (Direct Cost: ¥7,200,000)
Fiscal Year 1993: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1992: ¥3,700,000 (Direct Cost: ¥3,700,000)
KeywordsAcidic catalyst / Carboxylic ester / Glycosylation / 1,2-Cis glycoside / 2-Amino sugar / Ribose / Arabinose / 触媒的フリーデルクラフツ反応 / 触媒反応 / エステル化 / チオエステル / 芳香族ケトン / 対イオン
Research Abstract

In this research, new synthetic reactions using acitive acidic catalysts have been developed By using these novel catalysts, high efficiency has been attained.
1. In the presence of a catalytic amount of TiCl_4 and a stoichiometric amount of p-trifluoromethylbenzoic anhydride, aniline reacted with carboxylic acid trimethylsilylesters to give the corresponding carboxylic anilides in high yields.
2. In the presence of an active catalyst prepared from SiCl_4 and AgClO_4 and a stoichiometric amount of p-trifluoromethylbenzoic anhydride, carboxylic acids or their trimethylsilyl esters reacted with aromatic compounds to afford the corresponding Friedel-Crafts adducts in high yields.
3. In the presence of a catalytic amount of trityl salt, epoxides reacted with silylated nucleophiles to give the adducts, via carbon-carbon and carbon-oxygen bonds formation and rearrangement.
4. Several stereoselective glycosylation reactions of 2-amino sugars, arabinose, ribose, etc. were developed by using active catalysts under mild conditions.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] T.Mukaiyama: "An Efficient Synthesis of Unsymmetrical Sulfides from Organic Disulfides and Aromatic Compounds" Chemistry Letters. 1993. 1-4 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "Catalytic Stereoselective Synthesis of α-orβ-Ribofuranosides by Combined Use of Silver Salts and Lithium Perchlorate" Chemistry Letters. 1993. 781-784 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "Facile Synthesis of Lactones from Silyl ω-Siloxycarboxylates Using p-Trifluoromethyl benzoic Anhydride and a Catalytic Amount of Active" Chemistry Letters. 1993. 907-910 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Miyashita: "A Convenient Synthesis of Corboxanilides from Silyl Carboxylates and Weakly Nudeophilic Anilines Using p-Trifluoromethylbenzoic Anhydride" Bull.Chem.Soc.Jpn.67. 210-215 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] I.Shiina: "A Useful Method for the Preparation of Carboxylic Esters from Free Carboxylic Acids and Alcohols" Chemistry Letters. 1994. 515-518 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Suzuki: "The Catalytic Friedel-Crafts Acylation Reaction Starting from Aromatic Compound and Free Carboxylic Acids(or Their Trimethylsilyl Esters)" Bull.Chem.Soc.Jpn.66. 3729-3734 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "An Efficient Synthesis of Unsymmetrical Sulfides from Organic Disulfides and Aromatic Compounds" Chemistry Letters. 1993. 1-4 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "Catalytic Stereoselective Synthesis of alpha- or beta- Ribofuranosides by Combined Use of Silver Salts and Lithium Perchlorate of Diphenyltin Sulfide" Chemistry Letters. 1993. 781-784 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "Facile Synthesis of Lactones from Silyl omega- Siloxycarboxylates Using p-Torifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Lewis Acid" Chemistry Letters. 1993. 907-910 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Miyashita: "A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium(IV)" Bull. Chem. Soc. Jpn.67. 210-215 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] I.Shiina: "A Useful Method for the Preparation of Carboxylic Esters from Free Carboxylic Acids and Alcohols" Chemistry Letters. 1994. 515-518 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Suzuki: "The Catalytic Friedel-Crafts Acylation Reaction Starting from Aromatic Compounds and Free Carboxylic Acids (or Their Trimethylsilyl Esters) by Promotion of Silicon(IV) Cationic Species." Bull. Chem. Soc. Jpn.66. 3729-3734 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Mukaiyama: "An Efficient Synthesis of Unsymmetrical Sulfides from Organic Disulfides and Aromatic Compounds" Chemistry Letters. 1993. 1-4 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Mukaiyama: "Catalytic Stereoselective Synthesis of alpha- or beta-Ribofuranosides by Combined Use of Silver Salts and Lithium Perchlorate of Diphenyltin Sulfide" Chemistry Letters. 1993. 781-784 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Mukaiyama: "Facile Synthesis of Lactones from Silyl omega-Siloxycarboxylates Using P‐Torifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Lewis Acid" Chemistry Letters. 1993. 907-910 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Miyashita: "A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using P‐Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium(IV)" Bull.Chem.Soc.Jpn.67. 210-215 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] I.Shiina: "A Useful Method for the Preparation of Carboxylic Esters from Free Carboxylic Acids and Alcohols" Chemisty Letters. 1994. 515-518 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] K.Suzuki: "The Catalytic Friedel‐Crafts Acylation Reaction Starting from Aromatic Compounds and Free Carboxylic Acids(or their Trimethylsilyl Esters)by Promotion of Silicon(IV)Cationic Species" Bull.Chem.Soc.Jpn.66. 3729-3734 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] S.Kobayashi: "An Efficient Method for the Preparation of Chiral Synthons Starting from Racemic Compounds by Way of Asymmetric Synthesis" Chemistry Letters. 1992. 373-376 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "A Novel Catalyst System,Antimony(V)Chloride-Lithium Perchlorate (SbCl_<5-> LiClO_4),in the Friedel-Crafts Acylation Reaction" Chemistry Letters. 1992. 435-438 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "An Efficient Method for the Preparation of Carboxylic Esters via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid" Chemistry Letters. 1992. 625-628 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "Stereoselective Glycosylation Starting from 1-O-Trimethylsilyl Sugars by Using Diphenyltin Sulfide and a Catalytic Amount of Active Acidic Species" Chemistry Letters. 1992. 1041-1044 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "Stereoselective Synthesis of 1,2-cis-Arabinofuranosides Using a New Titanium Catalyst" Chemistry Letters. 1992. 1401-1404 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "A New and Efficient Method for the Preparation of S-Phenyl Carbothioates via Mixed Anhydrides Using Active Titanium(IV)Salts" Chemistry Letters. 1992. 1747-1750 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "An Efficient Catalytic Friedel-Crafts Acylation Reaction of Equimolar Amounts of Aromatic Compounds and Free Carboxylic Acids or their Trimethylsilylesters via Mixed Anhydrides" Chemistry Letters. 1992. 1751-1754 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "Stereoselective Synthesis of 2-Amino-2-deoxy-β-D-glucopyranosides and Galactopyranosides by Using a Catalytic Amount of Tin(II) Trifluoromethanesulfonate" Chemistry Letters. 1992. 1755-1758 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Harada: "A Convenient Method for the Preparation of Ethers from Epoxides.Trityl Hexafluoroantimonate-Catalyzed Sequential Reactions,Rearrangement and Reductive Condensation,of Epoxides" Chemistry Letters. 1992. 1901-1904 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount oF Active Species Generated from Methyltrichlorosilane and Silver Perchlorate" Chemistry Letters. 1992. 2105-2108 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Mukaiyama: "An Efficient Synthesis of Unsymmetrical Sulfides from Organic Disulfides and Aromatic Compounds" Chemistry Letters. 1993. 1-4 (1993)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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