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2008 Fiscal Year Final Research Report

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

Research Project

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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
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
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.

  • Research Products

    (34 results)

All 2009 2008 2007 2006 2005 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (17 results) Remarks (1 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

    • 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

    • 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

    • 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

    • 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

    • 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

    • 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

    • 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

    • 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

    • 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

    • Peer Reviewed
  • [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

    • 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

    • 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

    • 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 Backbone2005

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

      J. Am. Chem. Soc. 127

      Pages: 2548-2549

    • 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

    • 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

    • Peer Reviewed
  • [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
    • Year and Date
      20080907-20080910
  • [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
    • Year and Date
      20080303-20080305
  • [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
    • Year and Date
      20080107-20080108
  • [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
  • [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
    • Year and Date
      20071217-20071221
  • [Presentation] Binaphthyl-Modified Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      2nd ERA-Chemistry Flash Conference
    • Place of Presentation
      Evora, Portugal
    • Year and Date
      20071028-20071101
  • [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
    • Year and Date
      20070902-20070906
  • [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.
    • Year and Date
      20070715-20070720
  • [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
    • Year and Date
      20061217-20061221
  • [Presentation] Chiral Phase Transfer Catalysis for Practical Asymmetric Synthesis2006

    • Author(s)
      Maruoka, K.
    • Organizer
      Organocatalysis Symposium
    • Place of Presentation
      Tutzing, Germany
    • Year and Date
      20061008-20061011
  • [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.
    • Year and Date
      20060910-20060914
  • [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.
    • Year and Date
      20060611-20060615
  • [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
    • Year and Date
      20060607-20060609
  • [Presentation] Catalytic Asymmetric Synthesis with Designer Chiral Organocatalysts2006

    • Author(s)
      Maruoka, K.
    • Organizer
      7th Tetrahedron Symposium
    • Place of Presentation
      Kyoto Research Park, Kyoto, Japan
    • Year and Date
      20060525-20060526
  • [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
  • [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
    • Year and Date
      20051217-20051220
  • [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
    • Year and Date
      20051028-20051030
  • [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

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Published: 2011-06-18   Modified: 2016-04-21  

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