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2011 Fiscal Year Final Research Report

Development of Novel Chiral Bifunctional Phase-Transfer Catalyst and Its Application to Environmentally Benign Asymmetric Reactions

Research Project

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Project/Area Number 22750093
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

SHIRAKAWA Seiji  京都大学, 大学院・理学研究科, 准教授 (60459865)

Project Period (FY) 2010 – 2011
Keywords不斉合成 / 有機触媒 / 相間移動触媒 / 環境調和型反応 / 触媒開発 / 原子効率
Research Abstract

Asymmetric phase-transfer reaction is a powerful method for the efficient synthesis of biologically active compounds. Although many examples of chiral phase-transfer catalysts have been reported, truly efficient chiral phase-transfer catalyst is still limited. In this research, we have developed novel bifunctional phase-transfer catalysts for the asymmetric synthesis of useful compounds in drug development.

  • Research Products

    (21 results)

All 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (10 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Efficient Asymmetric Synthesis of a Bicyclic Amino Acid asa Core Structure of Telaprevir2012

    • Author(s)
      Shirakawa, S.; Liu, Y.; Usui, A.; Maruoka, K.
    • Journal Title

      ChemCatChem

      Volume: 4

    • DOI

      DOI:10.1002/cctc.201200081)

    • Peer Reviewed
  • [Journal Article] The Direct Catalytic A symmetric Aldol Reaction ofα-Substituted Nitroacetates with Aqueous Formaldehyde under Base-FreeNeutral Phase-Transfer Conditions2012

    • Author(s)
      Shirakawa, S.; Ota, K.; Terao, S. J.; Maruoka, K.
    • Journal Title

      Org. Biomol. Chem

      Volume: 10

    • DOI

      DOI:10.1039/C2OB07193B

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of Axially Chiral o-Iodoanilides by Phase-Transfer Catalyzed Alkylations2012

    • Author(s)
      Shirakawa, S.; Liu, K.; Maruoka, K
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 916-919

    • DOI

      DOI:10.1021/ja211069f

    • Peer Reviewed
  • [Journal Article] Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salt in Water-Rich Solvent2011

    • Author(s)
      Wang, L.; Shirakawa, S.; Maruoka, K
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 5327-5330

    • DOI

      DOI:10.1002/anie.201101307

    • Peer Reviewed
  • [Journal Article] Diastereo-and Enantioselective Conjugate Addition ofα-Substituted Nitroacetates to Maleimides under Base-Free Neutral Phase-Transfer Conditions2011

    • Author(s)
      Shirakawa, S.; Terao, S. J ; He, R.; Maruoka, K
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 10557-10559

    • DOI

      DOI:10.1039/c1cc14043d

    • Peer Reviewed
  • [Journal Article] Phase-Transfer Catalyzed Asymmetric Synthesis of1, 1-Disubstituted Tetrahydroisoquinolines2011

    • Author(s)
      Shirakawa, S.; Liu, K.; Ito, H.; Le, T. N.; Maruoka, K
    • Journal Title

      Adv. Synth. Catal

      Volume: 353 Pages: 2614-2618

    • DOI

      DOI:10.1002/adsc.201100269

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of 1, 1-Disubstituted Tetrahydro-β-carbolines by Phase-Transfer Catalyzed Alkylations2011

    • Author(s)
      Shirakawa, S.; Liu, K.; Ito, H.; Maruoka, K.
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 1515-1517

    • DOI

      DOI:10.1039/c0cc04447d

    • Peer Reviewed
  • [Presentation] Base-Free Neutral Phase-Transfer Reaction System2011

    • Author(s)
      Shirakawa, S.
    • Organizer
      Second International Collaborative and Cooperative Chemistry Symposium
    • Place of Presentation
      The University of Queensland,Queensland,Australia
    • Year and Date
      20111031-11
  • [Presentation] Phase-Transfer Catalyzed Asymmetric Synthesis of1, 1-Disubstituted Tetrahydro-β-carbolines and Tetrahydro isoquinolines2011

    • Author(s)
      Shirakawa, S.; Liu, K.; Ito, H.; Le, T. N.; Maruoka, K.
    • Organizer
      The 7th International Symposium on Intergrated Synthesis(ISIS-7)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      20111009-10
  • [Presentation] キラル相間移動触媒反応の新展開.塩基を用いない中性条件下での環境調和型キラル相間移動触媒反応.2011

    • Author(s)
      白川誠司
    • Organizer
      社団法人新化学技術推進協会先端化学・材料技術部会講演会
    • Place of Presentation
      東京
    • Year and Date
      2011-06-30
  • [Presentation] Asymmetric Phase-Transfer-Catalyzed Constructionof Quaetrnary Carbon Center in Chiral Cyclic Amines2011

    • Author(s)
      Liu, K.; Ito, H.; Shirakawa, S ; Maruoka, K.
    • Organizer
      5th Chem Comm International Symposium
    • Place of Presentation
      Kyoto University, Kyoto, Japan
    • Year and Date
      2011-05-16
  • [Presentation] Phase-Transfer Catalyzed Diastereoand Enantioselective Conjugate Additions ofα-Substituted Nitroacetates to Maleimides under Neutral Conditions2011

    • Author(s)
      Terao, S. J.; Shirakawa, S.; Maruoka, K
    • Organizer
      5th Chem Comm International Symposium
    • Place of Presentation
      Kyoto University, Kyoto, Japan
    • Year and Date
      2011-05-16
  • [Presentation] Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salt in Water-Rich Solvent2011

    • Author(s)
      Wang, L.; Shirakawa, S.; Maruoka, K.
    • Organizer
      5th Chem Comm International Symposium
    • Place of Presentation
      Kyoto University, Kyoto, Japan
    • Year and Date
      2011-05-16
  • [Presentation] Development of a Base-Free Chiral Phase-Transfer Reaction System2010

    • Author(s)
      Shirakawa, S.; Wang, L.; He, R.; Maruoka, K.
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] Practical Enantioselective Synthesisof Optically Active 1, 1-Disubstituted Tetrahydro-β-carbolines by Phase-Transfer-Ctalyzed Alkylation2010

    • Author(s)
      Liu, K.; Shirakawa, S.; Maruoka, K.
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20101215-20
  • [Presentation] Phase-Transfer Catalyzed Enantioselective Conjugate Additions ofα-Nitro Esters to Maleimides under Neutral Conditions2010

    • Author(s)
      Terao, S. J.; Shirakawa, S.; Maruoka, K.
    • Organizer
      The 6th International Symposium on Intergrated Synthesis(ISIS-6)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      20101023-24
  • [Presentation] Development of a Base-FreeChiral Phase-Transfer Reaction System2010

    • Author(s)
      Shirakawa, S.; Wang, L.; He, R.; Maruoka, K.
    • Organizer
      The 6th International Symposium on Intergrated Synthesis(ISIS-6)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      20101023-24
  • [Book] "Phase-Transfer Catalysis : Non-Natural-Product-Derived PTC" In Science of Synthesis : Asymmetric Organocatalysis 22012

    • Author(s)
      Shirakawa, S.; Maruoka, K.
    • Total Pages
      551-599
    • Publisher
      Georg Thieme Verlag
  • [Book] "Asymmetricα-Functionalization of Carbonyl Compounds and Alkylation of Enolates" In Science of Synthesis : Water in Organic Synthesis2012

    • Author(s)
      Shirakawa, S.; Maruoka, K.
    • Total Pages
      601-615
    • Publisher
      Georg Thieme Verlag
  • [Book] "Asymmetric Phase-Transfer and Ion Pair Catalysis" In CatalyticAsymmetric Synthesis2010

    • Author(s)
      Shirakawa, S.; Maruoka, K.
    • Total Pages
      95-117
    • Publisher
      John Wiley & Sons
  • [Remarks]

    • URL

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

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Published: 2013-07-31  

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