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Development of Asymmetric Reactions Catalyzed by Bronsted Acid in Aqueous Media

Research Project

Project/Area Number 12640528
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

AKIYAMA Takahiko  Faculty of Science, Department of Chemistry, Gakushuin University Professor, 理学部, 教授 (60202553)

Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2001: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2000: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsBronsted Acid / Mannich-type Reaction / β-Aminc Carbonyl Compounds / Diastereoselectivity / Schiff bases / Water / 立体選択性 / ブレンステッド酸 / β-アミノエステル / ケテンシリルアセタール / 水 / ジアステレオ選択性 / 不斉合成
Research Abstract

We have found that Mannich-type reactions took place smoothly under the influence of Bronsted acid, typically aq. HBF_4, to afford the corresponding (β-amino carbonyl compounds in high yields in aqueous organic solvents. Furthermore, the HBF_4-catalyzed Mannich-type reaction took place smoothly in the presence of sodium dodecyl sulfate in water under organic solvent-free conditions. Aza-Diels Alder reactions in aqueous media have been successfully achieved. Anti and syn stereoselectivity on the HBF_4-catalyzed Mannich-type reaction of ketene silyl acetal derived from α-oxy esters with aldimines were investigated. Whereas use of ketene silyl acetal derived from aryl ester in aqueous 2-propanol gave anti β-amino-α-siloxy ester with excellent stereoselectivity, use of ketene silyl acetal derived from methyl ester in water in the presence of sodium dodecyl sulfate gave the syn isomer preferentially.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] T.Akiyama, J.Takaya, H.Kagoshima: "Highly Stereo-divergent Mannich-type Reactions Catalyzed by Bronsted Acid in Aqueous Media"Tetrahedron Letters. 42・24. 4025-4028 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Akiyama, J.Takaya, H.Kagoshima: "Bronsted Acid Catalyzed Mannich-type Reactions in Aqueous Media"Advanced Synthesis & Catalysis. 343(印刷中). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H.Kagoshima, T.Uzawa, T.Akivama: "Catalytic, Enantioselective Propargyl-and Allenylation Reactions of α-lmino Esters"Chemistry Letters. 3. 288-290 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J.Takaya, H.Kagoshima, T.Akiyama: "Manich-type Reaction with Trifluoromethylateed N, O-Hemiacetal : Facile Preparation of β-Amino β-Trifluoromethyl Carbonyl Compounds"Organic Letters. 2・11. 1577-1579 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H.Kagoshima, T.Akiyama: "Novel [3+2] Cycloaddition of Alkenyl Fischer Carbene Complexes with Imines Leading to 3-Pyrroline Derivatives"Journal of American Chemical Society. 122・47. 11741-11742 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H.Kagoshima, T.Okamura, T.Akiyama: "The Asymmetric [3+2] Cycloaddition Reaction of Chiral Alkenyl Fischer Carbene Complexes with Imines: Synthesis of Optically Pure 2,5-Disubstituted-3-Pvrrolidinones"Journal of American Chemical Society. 123・29. 7182-7183 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Kagoshima, T. Uzawa, and T. Akiyama: "Catalytic, Enantioselective Propargyl- and Allenylation Reactions of α-Imino Esters"Chem. Lett.. 2002. 288-289

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Kagoshima, T. Okamura, and T. Akiyama: "The Asymmetric [3+2] Cycloaddition Reaction of Chiral Alkenyl Fischer Carbene Complexes with Imines: Synthesis of Optically Pure 2,5-Disubstituted-3-Pyrrolidinones"J. Am. Chem. Soc.. 123. 7182-7183 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Akiyama, J. Takaya, and H. Kagoshima: "Highly Stereo-Divergent Mannich-type Reaction Catalyzed by Bronsted Acid in Aqueous Media"Tetrahedron Lett.. 42. 4025-4028 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Akiyama, M. Sugano, and H. Kagoshima: "Lewis Acid-Mediated [3+2] Cycloaddition of Allyltriisopropylsilane to N-Sulfonyl Aldimines"Tetrahedron Lett.. 42. 3889-3992 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Kagoshima and T. Akiyama: "Novel [3+2] Cycloaddition Reaction of Alkenyl Fischer Carbene Complexes with Imines Leading to 3-Pyrroline Derivatives"J. Am. Chem. Soc.. 122. 11741-11742 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Takaya, H. Kagoshima, and T. Akiyama: "Mannich-type Reaction with Trifluoromethylated N,O-Hemiacetal; Facile Preparation of β-Amino-β-Trifluoromethyl Carbonyl Compounds"Org. Lett.. 2. 1577-1579 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Akiyama: "Development of Novel Synthetic Reactions Using Allylsilane"J. Synth. Org. Chem. Jpn.. 58. 285-292 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Akiyama, M. Suzuki, and H. Kagoshima: "Lewis Acid Promoted [4+2] Annulation of Allylsilane and Allylgermane with Aldimine; Preparation of Tetrahydroquinolines"Heterocycles. 52. 529-532 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Akiyama, I.Takaya, H.Kagoshima: "Highly Stereo-divergent Mannich-type Reactions Catalyzed by Bronsted Acid in Aqueous Media"Tetrahedron Letters. 42・24. 4025-4028 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Akiyama, J.Takaya, H.Kagoshima: "Bronsted Acid Catalyzed Mannich-type Reactions in Aqueous Media"Advanced Synthesis & Catalysis. 343(印刷中). (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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