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Development of Advanced Molecular Transformations of Functional Carbon Molecules using Fine Acid-Base Catalysts

Research Project

Project/Area Number 17065010
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionKyoto University

Principal Investigator

MARUOKA Keiji  Kyoto University, 大学院・理学研究科, 教授 (20135304)

Co-Investigator(Kenkyū-buntansha) OOI Takashi  京都大学, 大学院・理学研究科, 助教授 (80271708)
Project Period (FY) 2005 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥129,400,000 (Direct Cost: ¥129,400,000)
Fiscal Year 2008: ¥20,400,000 (Direct Cost: ¥20,400,000)
Fiscal Year 2007: ¥20,400,000 (Direct Cost: ¥20,400,000)
Fiscal Year 2006: ¥46,500,000 (Direct Cost: ¥46,500,000)
Fiscal Year 2005: ¥42,100,000 (Direct Cost: ¥42,100,000)
Keywords炭素資源 / 有機酸塩基触媒 / 高度分子変換 / プロセス有機合成化学 / キラル相間移動反応 / 光学活性アミノ酸 / 二官能基性有機触媒 / キラルジカルボン酸触媒 / キラル相間移動触媒 / キラル二官能性アミン触媒 / 不斉アミノ化反応 / 不斉マンニッヒ反応 / アルドール反応 / キラルジカルボン酸 / イミノアザエナミン反応 / 炭素炭素結合形成反応 / アミノ酸 / 不斉共役付加反応 / 不斉アルドール反応 / 不斉分子変換反応 / 二官能基性触媒 / 不斉ヒドロキシアミノ化 / スピロ型アンモニウム塩 / クラウンエーテル / 人工アミノ酸
Research Abstract

The development of excellent synthetic organic reactions to prepare important materials is urgent to Japan, where natural resources are scarce, as a scientific and technological country in order to keep the international superiority in the field of pharmaceutical and chemical industries. In this priority area, we utilize the readily accessible carbon resources efficiently, and pursuit new carbon-carbon bond-forming reactions based on the truly efficient molecular transformations. Namely, the field of asymmetric phase transfer chemistry, which is regarded as a desirable approach in process synthetic organic chemistry, has been exploited by using chiral binaphthyl-modified quaternary ammonium salts for the development of new, efficient asymmetric carbon-carbon bond-forming reactions. A rational design of chiral bifunctional organocatalysts and chiral dicarboxylic acid catalysts have been also realized for developing several new asymmetric methodologies.

Report

(5 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • Research Products

    (56 results)

All 2009 2008 2007 2006 2005 Other

All Journal Article (34 results) (of which Peer Reviewed: 22 results) Presentation (19 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Direct Asymmetric Benzoyloxylation of Aldehydes Catalyzed by 2-Tritylpyrrolidine2009

    • Author(s)
      Kano, T,; Mii, H.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 3450-3451

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Complete Switch of Product Selectivity in Asymmetric Direct Aldol Reaction with Two Different Chiral Organocatalysts from a Common Chiral Source2008

    • Author(s)
      Nakayama, K.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 17666-17667

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid2008

    • Author(s)
      Hashimoto, T.; Uchiyama, N.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 14380-14381

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Imino Aza-enamine Reaction Catalyzed by Axially Chiral Dicarboxylic Acid: Use of Arylaldehyde N, N-Dialkylhydrazones as Acyl Anion Equivalent2008

    • Author(s)
      Hashimoto, T.; Hirose, M.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 7556-7557

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design of an Axially Chiral Dicarboxylic Acid and Its Application in Syntheses of Optically Active β-Amino Acids and β-Amino Phosphonic Acid Derivatives2008

    • Author(s)
      Hashimoto, T.; Maruoka, K.
    • Journal Title

      Synthesis

      Pages: 3703-3706

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] 6, 6'-Substituent Effect of BINOL in Bis-Titanium Chiral Lewis Acid Catalyzed 1, 3-Dipolar Cycloaddition of Nitrones2008

    • Author(s)
      Hashimoto, T.; Omote, M.; Maruoka, K.
    • Journal Title

      Org. Biomol. Chem. 6

      Pages: 2263-2265

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bronsted Acid Catalyzed Insertion of Aryldiazoacetates to sp3 Carbon-CHO Bond : Facile Construction of Asymmetric All-Carbon Quaternary Center2008

    • Author(s)
      T.Hashimoto
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 2434-2435

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of Chiral Bifunctional Secondary Amine Catalysts for Asymmetric Enamine Catalysis2008

    • Author(s)
      T.Kano
    • Journal Title

      Chemical Communications

      Pages: 5465-5473

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid2008

    • Author(s)
      T.Hashimoto
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 14380-14381

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds2007

    • Author(s)
      Hashimoto, T.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 10054-10055

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Recent Development and Application of Chiral Phase-Transfer Catalysts2007

    • Author(s)
      Hashimoto, T.; Maruoka, K.
    • Journal Title

      Chem. Rev. 107

      Pages: 5656-5682

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] New, Chiral Phase Transfer Catalysts for Effecting Asymmetric Conjugate Additions of α-Alkyl-α-cyanoacetates to Acetylenic Esters2007

    • Author(s)
      Wang, X.; Kitamura, M.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 1038-1039

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Rearrangement of α, α-Disubstituted α-Siloxy Aldehydes to Optically Active Acyloins using Axially Chiral Organoaluminum Lewis Acids2007

    • Author(s)
      Ooi, T.; Ohmatsu, K.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 2410-2411

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] New, Chiral Phase Transfer Catalysts for Effecting Asymmetric Conjugate Additions of α-Alkyl-α-cyanoacetates to Acetylenic Esters2007

    • Author(s)
      X. Wang
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 1038-1039

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds2007

    • Author(s)
      T. Hashimoto
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 10054-10055

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] (19) syn-Selective and Enantioselective Direct Cross-Aldol Reactions between Aldehydes Catalyzed by an Axially Chiral Amino Sulfonamide2007

    • Author(s)
      T. Kano
    • Journal Title

      Angewandte Chemie International Edition 46

      Pages: 1738-1740

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New, Chiral Phase Transfer Catalysts for Effecting Asymmetric Conjugate Additions of α-Alkyl-α-cyanoacetates to Acetylenic Esters2007

    • Author(s)
      Xisheng Wang
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 1038-1038

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Direct Asymmetric Hydroxyamination Reaction Catalyzed by an Axially Chiral Secondary Amine Catalyst2006

    • Author(s)
      Kano, T.; Ueda, M.; Takai, J.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 6046-6047

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of New Chiral Quaternary Ammonium Salts with Tetranaphthyl Backbone2006

    • Author(s)
      Ooi, T.; Uematsu, Y.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 2548-2549

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective 1, 3-Dipolar Cycloaddition Reaction between Diazoacetates and α-Substituted Acroleins: Total Synthesis of Manzacidin A2006

    • Author(s)
      Kano, T.; Hashimoto, H.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 2174-2175

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase- Transfer Catalysis of New Chiral Quaternary Ammonium Salts with Tetranaphthyl Backbone2006

    • Author(s)
      Takashi Ooi
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 2548-2548

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Direct Asymmetric Hydroxyamination Reaction Catalyzed by an Axially Chiral Secondary Amine Catalyst2006

    • Author(s)
      Taichi Kano
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 6046-6046

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Construction of Enantiomerically Enriched Tertiary α-Hydroxycarboxylic Acid Derivatives by Phase-Transfer-Catalyzed Asymmetric Alkylation of Diaryloxazolidin-2, 4-diones2006

    • Author(s)
      Takashi Ooi
    • Journal Title

      Angewandte Chemie International Edition 45

      Pages: 3839-3839

    • Related Report
      2006 Annual Research Report
  • [Journal Article] exo-Selective Asymmetric Diels-Alder Reaction Catalyzed by Diamine Salts as Organocatalysts2006

    • Author(s)
      Taichi Kano
    • Journal Title

      Organic Letters 8

      Pages: 2687-2687

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Highly Diastereo- and Enantioselective Formal Conjugate Addition of Nitroalkanes to Nitroalkenes by Chiral Ammonium Bifluoride Catalysis2006

    • Author(s)
      Takashi Ooi
    • Journal Title

      Angewandte Chemie International Edition 45

      Pages: 7606-7606

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of New Chiral Quaternary Ammonium Salts with Tetranaphthyl Backbone2006

    • Author(s)
      Takashi Ooi
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 2548-2548

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Asymmetric Strecker Reaction of Aldimines Using Aqueous Potassium Cyanide by Phase-Transfer Catalysis of New Chiral Quaternary Ammonium Salts with Tetranaphthyl Backbone2005

    • Author(s)
      Ooi, T.; Uematsu, Y.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 2548-2549

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst2005

    • Author(s)
      Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 16408-16409

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected α-Amino Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, α-Amino Ketones, and α-Amino Alcohols2005

    • Author(s)
      Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 5073-5083

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Dramatic Rate Enhancement of Asymmetric Phase-Transfer-Catalyzed Alkylations2005

    • Author(s)
      Seiji Shirakawa
    • Journal Title

      Angewandte Chemie International Edition in English 44

      Pages: 625-625

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Powerful chiral Phase Transfer Catalysts for the Asymmetric Synthesis of a-Alkyl- and a, a-Dialkyl-a-amino Acids2005

    • Author(s)
      Masanori Kitamura
    • Journal Title

      Angewandte Chemie International Edition in English 44

      Pages: 1549-1549

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Highly Enantioselective Phase-Transfer-Catalyzed Alkylation of Protected a-Amino Acid Amides toward Practical Asymmetric Synthesis of Vicinal Diamines, a-Amino Ketones, and a-Amino Alcohols2005

    • Author(s)
      Takashi Ooi
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 5073-5073

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Design of an Axially Chiral Amino Acid with a Binaphthl Backbone as an Organocatalyst for a Direct Asymmetric Aldol Reaction2005

    • Author(s)
      Taichi Kano
    • Journal Title

      Angewandte Chemie International Edition in English 44

      Pages: 3055-3055

    • Related Report
      2005 Annual Research Report
  • [Journal Article] anti-Selective Direct Asymmetric Mannich Reactions Catalyzed by Axially Chiral Amino Sulfonamide as an Organocatalyst2005

    • Author(s)
      Taichi Kano
    • Journal Title

      Journal of the American Chemical Society 127

      Pages: 16408-16408

    • Related Report
      2005 Annual Research Report
  • [Presentation] Designer Chiral Organocatalysts for Catalytic Asymmetric Synthesis2008

    • Author(s)
      Maruoka, K.
    • Organizer
      International Workshop on Green Chemistry
    • Place of Presentation
      Hong Kong
    • Year and Date
      2008-04-28
    • Related Report
      2008 Final Research Report
  • [Presentation] Organocatalytic Way to the Asymmetric Synthesis of Useful Amino Acids and Alkaloid Derivatives2008

    • Author(s)
      Maruoka, K.
    • Organizer
      The 20th French-Japanese Symposium on Medicinal & Fine Chemistry
    • Place of Presentation
      Bordeaux, France
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Binaphthyl-Modified Chiral Organocatalysts for Asymmetric Synthesis2008

    • Author(s)
      Maruoka, K.
    • Organizer
      9th Netherlands Catalysis and Chemistry Conference
    • Place of Presentation
      Amsterdam, Netherland
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthetic Utility of Diazoacetates with Chiral Metal and Non-Metal Catalysts2008

    • Author(s)
      Maruoka, K.
    • Organizer
      First Japan-Singapore Bilateral Symposium on Catalysis
    • Place of Presentation
      Singapore
    • Related Report
      2008 Final Research Report
  • [Presentation] Organocatalytic Way to the Asymmetric Synthesis of Useful Amino Acids and Alkaloid Derivatives2008

    • Author(s)
      K.Maruoka
    • Organizer
      20th French-Japanese Symposium on Medicinal & Fine Chemistry
    • Place of Presentation
      Bordeaux, France
    • Related Report
      2008 Annual Research Report
  • [Presentation] Design of Chiral Bifunctional Organocatalysts for Asymmetric Organocatalysis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2007
    • Place of Presentation
      Singapore
    • Related Report
      2008 Final Research Report
  • [Presentation] Binaphthyl-Modified Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      2nd ERA-Chemistry Flash Conference
    • Place of Presentation
      Evora, Portugal
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      The 2nd International Conference on Cutting-Edge Organic Chemsitry
    • Place of Presentation
      Busan, Korea
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      Gordon Research Conference on Organic Reactions and Processes
    • Place of Presentation
      Rhode Island, U.S.A.
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      K. Maruoka
    • Organizer
      Gordon Research Conference on Organic Reactions and Processes
    • Place of Presentation
      Bryant University
    • Related Report
      2007 Annual Research Report
  • [Presentation] Chiral Designer Organocatalysts for Practical Asymmetric Synthesis2006

    • Author(s)
      Maruoka, K.
    • Organizer
      2006 Japan-Taiwan Joint Symposium on Organic Chemistry, Kyoto University
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2006-04-23
    • Related Report
      2008 Final Research Report
  • [Presentation] Practical Asymmetric Synthesis with Designer Chiral Organocatalysts2006

    • Author(s)
      Maruoka, K.
    • Organizer
      9th International Symposium for Chinese Organic Chemists (ISCOC-9)
    • Place of Presentation
      Grand Copthorne Waterfront Hotel Singapore, Singapore
    • Related Report
      2008 Final Research Report
  • [Presentation] Chiral Phase Transfer Catalysis for Practical Asymmetric Synthesis2006

    • Author(s)
      Maruoka, K.
    • Organizer
      Organocatalysis Symposium
    • Place of Presentation
      Tutzing, Germany
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Phase Transfer Catalysts for Practical Asymmetric Synthesis2006

    • Author(s)
      Maruoka, K.
    • Organizer
      Organocatalysis Synposium in the 232nd ACS National Meeting
    • Place of Presentation
      San Francisco, U.S.A.
    • Related Report
      2008 Final Research Report
  • [Presentation] Catalytic Asymmetric Synthesis with Chiral Designer Phase Transfer Catalysts2006

    • Author(s)
      Maruoka, K.
    • Organizer
      16th IUPAC's International Conference on Organic Synthesis (ICOS-16)
    • Place of Presentation
      Merida, Mexico.
    • Related Report
      2008 Final Research Report
  • [Presentation] Catalytic Asymmetric Synthesis with Designer Chiral Organocatalysts2006

    • Author(s)
      Maruoka, K.
    • Organizer
      Modern Synthetic Methods and Chiral Europe
    • Place of Presentation
      Palace Hotel, Burgenstock
    • Related Report
      2008 Final Research Report
  • [Presentation] Catalytic Asymmetric Synthesis with Designer Chiral Organocatalysts2006

    • Author(s)
      Maruoka, K.
    • Organizer
      7th Tetrahedron Symposium
    • Place of Presentation
      Kyoto Research Park, Kyoto, Japan
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Extremely Active Chiral Phase Transfer Catalyst for Practical Asymmetric Synthesis2005

    • Author(s)
      Maruoka, K.
    • Organizer
      Pacifichem 2005
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Powerful Chiral Phase Transfer Catalysts for Asymmetric Carbon-Carbon Bond Formation2005

    • Author(s)
      Maruoka, K.
    • Organizer
      10th International Chemical Conference in Taipei (ICCT 10)
    • Place of Presentation
      Hsinchu, Taiwan
    • Related Report
      2008 Final Research Report
  • [Book] Asymmetric Synthesis - The Essentials2006

    • Author(s)
      Keiji Maruoka
    • Total Pages
      388
    • Publisher
      WILEY-VCH
    • Related Report
      2006 Annual Research Report
  • [Remarks] 本特定領域研究ホームページ

    • URL

      http://kuchem.kyoto-u.ac.jp/yugo/www/index.html

    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://kuchem.kyoto-u.ac.jp/yugo/www/index.html

    • Related Report
      2007 Annual Research Report

URL: 

Published: 2005-04-01   Modified: 2023-01-13  

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