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2011 Fiscal Year Final Research Report

Development of Dynamic Asymmetric Organocatalysis and Their Mechanistic Studies

Research Project

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Project/Area Number 22750084
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionThe Institute of Physical and Chemical Research (2011)
Tokyo University of Agriculture and Technology (2010)

Principal Investigator

SOHTOME Yoshihiro  独立行政法人理化学研究所, 袖岡有機合成化学研究室, 研究員 (50431888)

Project Period (FY) 2010 – 2011
Keywords有機触媒 / 不斉合成 / 水素結合 / エントロピー / マイケル反応 / フェノール
Research Abstract

We have designed and developed 1, 3-diamine-tethered guanidine/bisthiourea organocatalysts for catalytic asymmetric 1, 4-additions including 1) Friedel-Crafts alkylation of phenols and 2) phospha-Michael reactions. Kinetic analyses using Eyring plots uncovered that differences in the activation entropies(ΔΔS^‡) play a principal role in the stereodiscrimination of the developed F-C reactions. We also found that, in the phospha-Michael reactions, either the monomeric or oligomeric active species of the catalyst can be utilized depending on the solvent system.

  • Research Products

    (13 results)

All 2012 2011 2010

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (6 results) Book (1 results)

  • [Journal Article] Organocatalytic Asymmetric Synthesis of N, N-Bis-Dihydrofuranyl-Hydroxyamines : A Cascade Reaction Involving Friedel-Crafts Alkylation, Internal Redox Reaction and Umpolung2011

    • Author(s)
      Yoshihiro Sohtome, Takahisa Yamaguchi, Bongki Shin, Kazuo Nagasawa
    • Journal Title

      Chem. Lett

      Volume: 40 Pages: 843-845

    • Peer Reviewed
  • [Journal Article] Enantioselective Phospha-Michael Reaction of Diphenyl Phosphite with Nitroolefins Utilizing Conformationally Flexible Guanidine/Bisthiourea Organocatalyst : Assembly-State Tunability in Asymmetric Organocatalysis2011

    • Author(s)
      Yoshihiro Sohtome, Natsuko Horitsugi, Rika Takagi, Kazuo Nagasawa
    • Journal Title

      Adv. Synth. Catal.

      Volume: 353 Pages: 2631-2636

    • Peer Reviewed
  • [Journal Article] Linking the Conformational Flexibility and Kinetics : Catalytic 1, 4-Type Friedel-Crafts Reaction of Phenols Utilizing 1, 3-Diamine-Tethered-Guanidine/Bisthiourea Organocatalysts2011

    • Author(s)
      Yoshihiro Sohtome, Bongki Shin, Natsuko Horitsugi, Keiichi Noguchi, Kazuo Nagasawa
    • Journal Title

      Chem. Asian. J.

      Volume: 6 Pages: 2463-2470

    • Peer Reviewed
  • [Journal Article] Solvent-Dependent Enantiodivergent Mannich-Type Reaction : Utilizing Conformational Flexible Guanidine/Bisthiourea Organocatalyst2010

    • Author(s)
      Yoshihiro Sohtome, Shinji Tanaka, Keisuke Takada, Takahisa, Yamaguchi, Kazuo Nagasawa
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 9254-9257

    • Peer Reviewed
  • [Journal Article] Entropy-Controlled Catalytic Asymmetric 1, 4-Type Friedel-Crafts Reaction of Phenols Using A Conformationally Flexible Guanidine/Bisthiourea Organocatalyst2010

    • Author(s)
      Yoshihiro Sohtome, Shin Bongki, Natsuko Horitsugi, Rika Takagi, Keiichi Noguchi, Kazuo Nagasawa
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 7299-7303

    • Peer Reviewed
  • [Journal Article] The Design of Chiral Double Hydrogen Bonding Networks and Their Applications to Catalytic Asymmetric Carbon. Carbon and Carbon. Oxgen Bond. Forming Reactions2010

    • Author(s)
      Yoshihiro Sohtome, Kazuo Nagasawa
    • Journal Title

      Synlett

      Pages: 1-22

    • Peer Reviewed
  • [Presentation] 鎖状グアニジニン/チオウレア触媒の分子設計に基づく触媒機能の開拓研究2012

    • Author(s)
      五月女宜裕
    • Organizer
      第25回若い世代の特別講演会(日本化学会第91春季年会)
    • Place of Presentation
      慶応義塾大学理工学部
    • Year and Date
      2012-03-25
  • [Presentation] Asymmetric Cycle-Specific Catalysis Utilizing a 1, 3-Diamine-Tethered Guanidine/Bisthiourea Organocatalyst2011

    • Author(s)
      Yoshihiro Sohtome, Kazuo Nagasawa
    • Organizer
      The 6th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Hong Kong, The Chinese University of Hong Kong
    • Year and Date
      20111212-15
  • [Presentation] 1, 3-ジアミン型グアニジン/ビスチオウレア触媒の創製:触媒的不斉Friedel-Crafts反応及びカスケード反応への展開2011

    • Author(s)
      五月女宜裕、山口昂久、堀次奈津子、申峰基、長澤和夫
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島県あわぎんホール
    • Year and Date
      20111107-08
  • [Presentation] 環境応答性有機触媒の多次元制御2011

    • Author(s)
      五月女宜裕
    • Organizer
      理研シンポジウム
    • Place of Presentation
      理化学研究所、鈴木梅太郎ホール
    • Year and Date
      2011-07-01
  • [Presentation] Solvent-Dependent Enantiodivergent Mannich-Type Reaction Utilizing Conformationally Flexible Guanidine/Bisthiourea Organocatalyst2010

    • Author(s)
      Yoshihiro Sohotme, Shinji Tanaka, Kazuo Nagasawa
    • Organizer
      ISCD2010
    • Place of Presentation
      北海道、札幌コンベンションセンター
    • Year and Date
      2010-07-14
  • [Presentation] 新規鎖状グアニジン/チオウレア触媒の創製:ニトロオレフィン類の触媒的不斉1, 4-付加反応2010

    • Author(s)
      五月女宜裕、申峰基、堀次奈津子、高城梨夏、長澤和夫
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部
    • Year and Date
      2010-06-18
  • [Book] Chiral Guanidine and Amidine Organocatalysts in Science of Synthesis Reference Library, Asymmetric Organocatalysis 2 ; Bronsted Base and Acid Catalysts, and additional Topics2012

    • Author(s)
      Kazuo Nagasawa, Yoshihiro Sohtome
    • Total Pages
      1-40

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Published: 2013-07-31  

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