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INVENTION AND CHIRALITY-RECOGNITION ABILITY OF RESOLVING AGENTS HAVING A CHIRAL FUNCTIONAL GROUP AND ITS MECHANISM

Research Project

Project/Area Number 19350064
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

SAIGO Kazuhiko  The University of Tokyo, 大学院・工学系研究科, 教授 (80016154)

Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥15,600,000 (Direct Cost: ¥12,000,000、Indirect Cost: ¥3,600,000)
Fiscal Year 2009: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2008: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2007: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywordsジアステレオマー塩 / 光学分割 / キラル識別能 / チオホスホン酸 / チオホスフィン酸 / N-キラルモノアミン / X-線結晶構造解析 / 計算機化学手法 / キラル識別機構 / ハロゲン相互作用 / 分子長原則 / キラルリン化合物 / キラル窒素化合物 / キラリティー識別能 / ハロゲン相互作 / 結晶工学 / 分子認識 / キラル認識 / 中心性キラリティー / 水素結合 / キラル識別
Research Abstract

We developed several kinds of enantiopure phosphonothioic and phosphinothioic acids as new resolving agents having a chiral functional group. They showed a unique chirality-recognition ability to racemic amines and amino alcohols, depending on their chemical structure. Moreover, the X-ray crystallography of the diastereomeric salts revealed that halogen interaction plays an important role for the stabilization of less-soluble diastereomeric salt crystals other than hydrogen-bonding, CH/π, and van der Waals interactions. On the other hand, the present study suggested that the synthesis of compounds having a chiral tertiary amino group is not so difficult that they would be a new series of resolving agents with a chiral functional group.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (23 results)

All 2010 2009 2008 2007

All Journal Article (18 results) (of which Peer Reviewed: 8 results) Presentation (5 results)

  • [Journal Article] Halogen-Bonding Interaction Stabilizing Cluster-type Diastereomeric Salt Crystals2010

    • Author(s)
      Y. Kobayashi, J. Maeda, T. Ando, K. Saigo
    • Journal Title

      Crystal Growth & Design 19360003

      Pages: 685-690

    • Related Report
      2009 Final Research Report
  • [Journal Article] Synthesis and isolation of a monoamine having a thermodynamically stabilized pseudo-chirotopic nitrogen2009

    • Author(s)
      Y. Kobayashi, K. Sano, K. Saigo
    • Journal Title

      Tetrahedron Lett.

      Pages: 799-801

    • Related Report
      2009 Final Research Report
  • [Journal Article] Enantiopure Cyclic 0-Substituted Phenylphosphonothioic Acid : Synthesis and Chirality-Recognition Ability2009

    • Author(s)
      N. Ribeiro, Y. Kobayashi, J. Maeda, K. Saigo
    • Journal Title

      Chirality

    • Related Report
      2009 Final Research Report
  • [Journal Article] Enantiopure tert-butyl (phenyl) phosphine oxide2009

    • Author(s)
      N. Ribeiro, K. Saigo
    • Journal Title

      Chirality-recognition ability and mechanism, Tetrahedron : Asymmetry 20

      Pages: 2704-2708

    • Related Report
      2009 Final Research Report
  • [Journal Article] Halogen-Bonding Interaction Stabilizing Cluster-type Diastereomeric Salt Crystals2009

    • Author(s)
      小林由佳, 前田仁, 安藤哲雄, 西郷和彦
    • Journal Title

      Tetrahedron Letters 50

      Pages: 799-801

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiopure Cyclic O-Substituted Phenylphosphonothioic Acid : Synthesis and Chirality-Recognition Ability2009

    • Author(s)
      Nigel Ribeiro, 小林由佳, 前田仁, 西郷和彦
    • Journal Title

      Chirality 1(DOI : 10.1002/20702)

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiopure tert-butyl(phenyl)phosphine oxide. Chirality-recognition ability and mechanism2009

    • Author(s)
      Nigel Ribeiro, 西郷和彦
    • Journal Title

      Tetrahedron : Asymmetry 20

      Pages: 2704-2708

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and isolation of a monoamine having a thermodynamically stabilized pseudo-chirotopic nitrogen2009

    • Author(s)
      Yuka Kobayashi, Kentaro Sano, Kazuhiko Saigo
    • Journal Title

      Tetrahedron Letters 50

      Pages: 799-801

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiopure cyclic O-substituted phenylphosphonothioic acid: Synthesis and chirality-recognition ability2009

    • Author(s)
      Nigel Ribeiro, Yuka Kobayashi, Jin Maeda, Kazuhiko Saigo
    • Journal Title

      Chirality 21(印刷中(掲載確定))

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1, 2-amino alcohol and an achiral carboxylic acid2008

    • Author(s)
      Y. Kobayashi, Soetrisno, K. Kodama, K. Saigo
    • Journal Title

      Tetrahedron : Asymmetry 19

      Pages: 295-301

    • Related Report
      2009 Final Research Report
  • [Journal Article] Factors determining the pattern of a hydrogen-bonding network in the diastereomeric salts of 1-arylethylamines with enantiopure P-chiral acids2008

    • Author(s)
      Y. Kobayashi, H. Handa, J. Maeda, K. Saigo
    • Journal Title

      Chirality 20

      Pages: 577-584

    • Related Report
      2009 Final Research Report
  • [Journal Article] Hydrogen-bonding sheets in crystals for chirality-recognition : synthesis and application of (2S, 3S)-2, 3-dihydroxy- and (2S, 3S)-2, 3-dibenzyloxy-1, 4-bis (hydro xyamino) butanes2008

    • Author(s)
      Y. Kobayashi, Y. Kokubo, T. Aisaka, K. Saigo
    • Journal Title

      Tetrahedron : Asymmetry 19

      Pages: 2536-2541

    • Related Report
      2009 Final Research Report
  • [Journal Article] Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy-and (2S,3S)-2,3-dibenzyloxy-1,4-bis (hydroxyamino)butanes2008

    • Author(s)
      Yuka Kobayashi, Yasushi Kokubo, Takamitsu Aisaka, Kazuhiko Saigo
    • Journal Title

      Tetrahedron: Asymmetry 19

      Pages: 2536-2541

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular herical channel consisting of an enantiopure 1,2-amino alcohols and an achiral carboxylic acid2008

    • Author(s)
      小林 由佳, Soetrisno, 小玉 康一, 西郷 和彦
    • Journal Title

      Tetrahedron:Asymmetry 19

      Pages: 295-301

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Factors Determining the Pattern of a Hydrogen-Bonding Network in the Diastereomeric Salts of 1-Arylethylamines with Enantiopure P-Chiral Acids2008

    • Author(s)
      小林 由佳, 半田 博章, 前田 仁, 西郷 和彦
    • Journal Title

      Chirality 20

      Pages: 577-584

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Unusual Demethylation of 0, 0'-Dimethyl Chlorothiophosphate with Aryllithiums2007

    • Author(s)
      N. Ribeiro, J. Maeda, Y. Ishida, Y. Kobayashi, K. Saigo
    • Journal Title

      Chem. Lett. 36

      Pages: 1412-1413

    • Related Report
      2009 Final Research Report
  • [Journal Article] The role of CH/π interaction in the stabilization of less-soluble diastereomeric salt crystals2007

    • Author(s)
      K. Saigo, Y. Kobayashi
    • Journal Title

      Chem. Rec. 7

      Pages: 47-56

    • Related Report
      2009 Final Research Report
  • [Journal Article] Role of the relative molecular length on the components in ternary inclusion crystals in the chiral recognition and assembly of supramolecular helical architectutes2007

    • Author(s)
      K. Kodama, Y. Kobayashi, K. Saigo
    • Journal Title

      Crystal Growth & Design 7

      Pages: 935-939

    • Related Report
      2009 Final Research Report
  • [Presentation] 嵩高い第一級キラルアミンの合成とそのキラル識別能2009

    • Author(s)
      安藤哲雄・小林由佳・伊藤宏・西郷和彦
    • Organizer
      日本化学会第89春期年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] キラル二成分結晶を用いた不均-系不斉反応の開発2009

    • Author(s)
      松本華子・小林由佳・伊藤宏・西郷和彦
    • Organizer
      日本化学会第89春期年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] Enantiopure Cyclic Phenylphosphonothioic Acid: Synthesis and Chirality Recognition Ability2008

    • Author(s)
      Nigel Ribeiro,・小林由佳・前田仁・西郷和彦
    • Organizer
      シンポジウム モレキュラー・キラリティー2008
    • Place of Presentation
      岡山大学創立五十周年記念館
    • Year and Date
      2008-05-22
    • Related Report
      2008 Annual Research Report
  • [Presentation] 嵩高い第一級キラルアミンの創製とそのキラル識別能2008

    • Author(s)
      安藤哲雄・小林由佳・伊藤宏・西郷和彦
    • Organizer
      シンポジウム モレキュラー・キラリティー2008
    • Place of Presentation
      岡山大学創立五十周年記念館
    • Year and Date
      2008-05-22
    • Related Report
      2008 Annual Research Report
  • [Presentation] キラルリン(V)化合物を用いるキラル識別2008

    • Author(s)
      半田 博章, 小林 由佳, 西郷 和彦
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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