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Study of Environmentally Friendly Organic Synthesis Based on High Pressure Reactions

Research Project

Project/Area Number 14204072
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field 物質変換
Research InstitutionKochi University

Principal Investigator

KOTSUKI Hiyoshizo  Kochi University, Faculty of Science Department of Materials Science, Professor, 理学部, 教授 (80093954)

Co-Investigator(Kenkyū-buntansha) YANAGISAWA Kazumichi  Kochi University, Faculty of Science Lab of Hydrothermal Chemistry, Professor, 理学部, 教授 (90145110)
ICHIKAWA Yoshiyasu  Kochi University, Faculty of Science Department of Materials Science, Professor, 理学部, 教授 (60193439)
GAMOH Keiji  Kochi University, Faculty of Education Department of Chemistry, Professor, 教育学部, 教授 (90204817)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥56,160,000 (Direct Cost: ¥43,200,000、Indirect Cost: ¥12,960,000)
Fiscal Year 2004: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000)
Fiscal Year 2003: ¥14,430,000 (Direct Cost: ¥11,100,000、Indirect Cost: ¥3,330,000)
Fiscal Year 2002: ¥33,150,000 (Direct Cost: ¥25,500,000、Indirect Cost: ¥7,650,000)
KeywordsHigh Pressure Reactions / Solvent-Free Reactions / Uncatalyzed Reactions / Hydrothermal Reactions / Asymmetric Organocatalysis / Condensation Reactions / Natural Product Synthesis / Organic Materials Synthesis / pincer-Diels-Alder反応 / 無触媒的アセタール化反応 / 無触媒的縮合反応 / 不斉アルドール反応 / 生理活性天然物合成 / 有機不斉塩基触媒 / 不斉Michael付加反応 / 水熱反応 / Diels-Alder反応 / 脱水縮合反応 / 芳香環アルキル化 / D化反応 / 異性化反応 / 還元的二量化 / 水中反応
Research Abstract

1.Diels-Alder Reaction of Less Reactive Dienes under High-Pressure/Solvent Free Conditions :
Dramatic effects of high-pressure/solvent-free conditions were recognized for the Diels Alder reaction of thiophene. Under the very similar conditions, domino- and pincer-Diels-Alder reactions of furan were performed. All of these adducts were not easily prepared by other means. From the viewpoint of atom economy these provide a unique method in organic synthesis.
2.Uncatalyzed Functional Group Transformations under High-Pressure/Solvent-Free Conditions :
Several important methods for the functional group transformations were developed under high-pressure/solvent-free conditions in the absence of any catalysts. For example, the synthesis of pyridine-thiourea conjugates via condensation between isothiocyanates and aminopyridines, acetalization of ketones, synthesis of substituted ureas via condensation of trichloroethylcarbamates with amines, Strecker reaction using aromatic ketones/aromatic amines … More / trirnethylsilyl cyanide.
3.Novel Synthesis of Nitrogen Heterocycles via Condensation of Ketones under Hydrothermal Conditions :
Cyclocondensation of cyclic ketones in hot aqueous ammonium chloride gave fully substituted pyridine derivatives in good yields. On the other hand, treatment of o-phenylaniline hydrochloride salts with cyclic ketones in hot water produced phenanthridine derivatives in good yields. These are all typical examples of novel use of hydrothermal chemistry in organic synthesis and contribute to the development of environmentally friendly organic synthesis.
4.Aromatic H-D Exchange Reactions under Hydrothermal Conditions in D20 :
The efficient method for H-D exchange reactions of aromatic amines was developed by conducting the reactions in D2O under hydrothermal conditions.
5.Development of Novel Asymmetric Organocatalysts :
Novel synthesis of chiral pyrrolidine-pyridine conjugate base catalysts was performed, and these catalysts were applied for the asymmetric Michael addition reaction of ketones with nitroolefins. The results were excellent in view of catalytic activity, diastereoselectivity, and enantioselectivity.
6.Organocatalytic Asymmetric Synthesis of Natural Products :
Novel straight chain aliphatic aldehyde synthons were developed for the use in L-proline catalyzed asymmetric aldol reactions. The utility of this method was exemplified by the short synthesis of oviposition attractant pheromone, sphyngosines, boronolide in optically pure forms.
7.Miscellaneous Organic Functional Group Transformations:
Cis/traps isomerization of 4-substituted cylohexylbenzene derivatives, liquid crystalline materials, under the catalysis of TfOH. Less

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (51 results)

All 2005 2004 2003 2002 Other

All Journal Article (21 results) Book (10 results) Patent(Industrial Property Rights) (9 results) Publications (11 results)

  • [Journal Article] Multicomponent Strecker Reaction under High Pressure2005

    • Author(s)
      K.Matsumoto, 他6名
    • Journal Title

      Helvetica Chimica Acta (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 超高圧有機合成化学における最近の進歩2005

    • Author(s)
      小槻日吉三, 隈本康司
    • Journal Title

      有機合成化学協会誌 (印刷中)

    • NAID

      10016680544

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 超高圧有機合成化学における最近の進歩2005

    • Author(s)
      小槻日吉三, 隈本康司
    • Journal Title

      有機合成化学協会誌 63(印刷中)

    • NAID

      10016680544

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Diels-Alder Reaction of Thiophene : Dramatic Effects of High-Pressure/Solvent-Free Conditions2004

    • Author(s)
      K.Kumamoto, 他2名
    • Journal Title

      Angewandte Chemie International Edition 43

      Pages: 2015-2017

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effects of Porphyrins on Encystment and Excystment in Ciliated Protozoan Colpoda sp.2004

    • Author(s)
      S.Tsutsumi, 他4名
    • Journal Title

      Japanese Journal of Protozoology 37

      Pages: 119-126

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A New Class of Chiral Pyrrolidine-Pyridine Conjugate Base Catalysts for Use in Asymmetric Michael Addition Reactions2004

    • Author(s)
      T.Ishii, 他3名
    • Journal Title

      Journal of the American Chemical Society 124

      Pages: 9558-9559

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diels-Alder Reaction of Thiophene : Dramatic Effects of High-Pressure/Solvent-Free Conditions2004

    • Author(s)
      K.Kumamoto
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 2015-2017

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effects of Porphyrins on Encystment and Excystment in Ciliated Protozoan Colpoda sp.2004

    • Author(s)
      S.Tsutsumi
    • Journal Title

      Jpn.J.Protozool. 37

      Pages: 119-126

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A New Class of Chiral Pyrrolidine-Pyridine Conjugate Base Catalysts for Use in Asymmetric Michael Addition Reactions2004

    • Author(s)
      T.Ishii
    • Journal Title

      J.Am.Chem.Soc. 124

      Pages: 9558-9559

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diels-Alder Reaction of Thiophene : Dramatic Effects of High-Pressure/ Solvent-Free Conditions2004

    • Author(s)
      K.Kumamoto 他2名
    • Journal Title

      Angewandte Chemie International Edition 43

      Pages: 2015-2017

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Class of Chiral Pyrrolidine-Pyridine Conjugate Base Catalysts for Use in Asymmetric Michael Addition Reactions2004

    • Author(s)
      T.Ishii 他3名
    • Journal Title

      Journal of the American Chemical Society 124

      Pages: 9558-9559

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Unprecedented Hydrothermal Reaction of o-Phenylaniline and Related Derivatives with Cyclic Ketones. A Novel Approach to the Construction of Phenanthridine and Quinoline Ring Systems2003

    • Author(s)
      B.K.Mehta, 他3名
    • Journal Title

      Organic Letters 5

      Pages: 1605-1608

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] High-Pressure-Promoted Asymmetric Aldol Reactions of Ketones with Aldehydes Catalyzed by L-Proline2003

    • Author(s)
      Y.Sekiguchi, 他4名
    • Journal Title

      Synlett 2003

      Pages: 1655-1658

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Hypothetical Photosensory Structure and Transduction in Ciliated Protozoan, Blepharisma2003

    • Author(s)
      A.Kida, 他
    • Journal Title

      Trends in Photochemistry & Photobiology 10

      Pages: 93-101

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Unprecedented Hydrothermal Reaction of o-Phenylaniline and Related Derivatives with Cyclic Ketones. A Novel Approach to the Construction of Phenanthridine and Quinoline Ring Systems2003

    • Author(s)
      B.K.Mehta
    • Journal Title

      Org.Lett. 5

      Pages: 1605-1608

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] High-Pressure-Promoted Asymmetric Aldol Reactions of Ketones with Aldehydes Catalyzed by L-Proline2003

    • Author(s)
      Y.Sekiguchi
    • Journal Title

      Synlett

      Pages: 1655-1658

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Hypothetical Photosensory Structure and Transduction in Ciliated Protozoan, Blepharisma2003

    • Author(s)
      A.Kida
    • Journal Title

      Trends in Photochem.Photobiol. 10

      Pages: 93-101

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] High-pressure-promoted Condensation of Isothiocyanates with Aminopyridines : Efficient Synthesis of Pyridine-thiourea Conjugates as Building Blocks for Hydrogen-bonding Receptors2002

    • Author(s)
      K.Kumamoto, 他4名
    • Journal Title

      Tetrahedron Letters 43

      Pages: 1035-1038

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] High-pressure-promoted Condensation of Isothiocyanates with Aminopyridines : Efficient Synthesis of Pyridine-thiourea Conjugates as Building Blocks for Hydrogen-bonding Receptors2002

    • Author(s)
      K.Kumamoto
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 1035-1038

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Multicomponent Strecker Reaction under High Pressure

    • Author(s)
      K.Matsumoto
    • Journal Title

      Helv.Chim.Acta (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Recent Advances in High Pressure Organic Synthesis

    • Author(s)
      H.Kotsuki
    • Journal Title

      Yuki Gosei Kagaku Kyokai-shi (in press)

    • NAID

      10016680544

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] 実験化学講座 第5版,第6巻2005

    • Author(s)
      小槻日吉三
    • Publisher
      丸善(印刷中)
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Book] Jikkenn Kagaku Koza, 5th Ed., Vol.62005

    • Author(s)
      Nihon Kagaku Kai
    • Publisher
      Maruzen(in press)
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] 化学便覧、基礎編、改訂第5版2004

    • Author(s)
      小槻日吉三
    • Publisher
      丸善
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] 化学研究 生中継2004

    • Author(s)
      小槻日吉三
    • Publisher
      南の風社
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] Kagaku Kenkyu Nama-chukei2004

    • Author(s)
      Kochi Univ.
    • Publisher
      Minamino Kaze Sha
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] My Favorite Organic Synthesis2002

    • Author(s)
      小槻日吉三
    • Publisher
      有機合成化学協会
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] 光高圧機器 高圧研究機器設計図集2002

    • Author(s)
      小槻日吉三
    • Publisher
      光高圧機器「高圧研究機器設計図集」出版会
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] My Favorite Organic Synthesis2002

    • Publisher
      Yuki Gosei Kagaku Kyokai
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] The Collection of Blueprints of High Pressure Apparatus Desinged

    • Author(s)
      Hikari Koatsu
    • Publisher
      Hikari Koatsu Kiki Shuppan Kai
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] Kagaku Binran, Kiso-hen, 5th Ed.

    • Author(s)
      Nihon Kagaku Kai
    • Publisher
      Maruzen
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 光学活性アミノピリジル基含有ピロリジン誘導体及びそれを用いた不斉合成方法2004

    • Inventor(s)
      小槻日吉三
    • Industrial Property Rights Holder
      国立大学法人高知大学
    • Industrial Property Number
      2004-210403
    • Filing Date
      2004-07-16
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 産卵誘引フェロモンの製造方法およびその製造中間体の製造方法2004

    • Inventor(s)
      小槻日吉三
    • Industrial Property Rights Holder
      国立大学法人高知大学
    • Industrial Property Number
      2004-220511
    • Filing Date
      2004-07-28
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] チオフェン誘導体及びその製造方法

    • Inventor(s)
      小槻 日吉三他1名
    • Industrial Property Rights Holder
      三井化学
    • Industrial Property Number
      2003-029864
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] トランスシクロヘキサン誘導体の製造方法

    • Inventor(s)
      小槻 日吉三他1名
    • Industrial Property Rights Holder
      ナガセケムテックス
    • Industrial Property Number
      2003-051597
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 光学活性ピロリジン誘導体

    • Inventor(s)
      小槻 日吉三
    • Industrial Property Rights Holder
      ナガセケムテックス
    • Industrial Property Number
      2003-075905
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] チオフェン誘導体の製造方法

    • Inventor(s)
      小槻 日吉三他1名
    • Industrial Property Rights Holder
      三井化学
    • Patent Publication Number
      2003-192687
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] チオフェン誘導体の製造方法

    • Inventor(s)
      小槻 日吉三他1名
    • Industrial Property Rights Holder
      三井化学
    • Patent Publication Number
      2003-192688
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 光学活性アミノピリジル基含有ピロリジン誘導体及びそれを用いた不斉合成方法

    • Inventor(s)
      小槻 日吉三
    • Industrial Property Rights Holder
      高知大学
    • Industrial Property Number
      2004-210403
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 産卵誘引フェロモンの製造方法およびその製造中間体の製造方法

    • Inventor(s)
      小槻 日吉三
    • Industrial Property Rights Holder
      高知大学
    • Industrial Property Number
      2004-220511
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] B.K.Mehta, 他3名: "Unprecedented Hydrothermal Reaction of o-Phenylaniline and Related Derivatives with Cyclic Ketones. A Novel Approach to the Construction of Phenanthridine and Quinoline Ring Systems"Organic Letters. Vol.5. 1605-1608 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Sekiguchi, 他4名: "High-Pressure-Promoted Asymmetric Aldol Reactions of Ketones with Aldehydes Catalyzed by L-Proline"Synlett. No.11. 1655-1658 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Kumamoto, 他2名: "Diels-Alder Reaction of Thiophene : Dramatic Effects of High-Pressure / Solvent-Free Conditions"Angewandte Chemie International Edition. Vol.43(in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 小槻 日吉三: "化学便覧、基礎編、改訂第5版(分担執筆)"丸善. (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 小槻 日吉三: "実験化学講座 第5巻"丸善(印刷中). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] B.K.Mehta, 他3名: "Unprecedented Hydrothermal Reaction of o-Phenylaniline and Related Derivatives with Cyclic Ketones. A Novel Approach to the Construction of Phenanthridine and Quinoline Ring Systems"Organic Letters. Vol.5(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Kumamoto, 他4名: "High-pressure-promoted Condensation of Isothiocyanates with Aminopyridines : Efficient Synthesis of Pyridine-thiourea Conjugates as Building Blocks for Hydrogen-bonding Receptors"Tetrahedron Letters. 43. 1035-1038 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Hiyoshizo Kotsuki: ""My Favorite Organic Synthesis", pp 88-89"化学同人. 253 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 小槻日吉三: "「光高圧機器 高圧研究機器設計図集」,pp128-129"光高圧機器「高圧研究機器設計図集」出版会. 173 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 小槻日吉三: "化学便覧、基礎編、改訂第5版"丸善(印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 小槻日吉三: "実験化学講座、第5巻"丸善(印刷中). (2004)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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