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Solid State Asymmetric Synthesis using A New Chiral Porous Metal-Organic Frame Work

Research Project

Project/Area Number 17550109
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKansai University

Principal Investigator

TANAKA Koichi  Kansai Univ., Faculty of Enginnering., Prof., 工学部, 教授 (10116949)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2006: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2005: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsPorous Metal-Organic Frame Work / Chirality / Solid State Reaction / Asymmetric Reaction / Solvent-free Reaction / Cyclohexenoxide / Aniline / Crystal Structure / 固相反応 / 不斉合成 / 反応場 / 超分子化学 / 分子認識 / 自己組織化 / ナノ材料 / 合成化学 / 包接
Research Abstract

A new porous chiral metal-organic framework (2) has been synthesized by treating axially chiral 2,2'-dihydroxy-1,1'-binaphthyl-5,5'-dicarboxylic acid (1) with Cu salts and its crystal structure has been elucidated by X-ray analysis. The porous chiral metal-organic framework (2) includes two MeOH molecules in the square cavity (15Åx15Å) constructed by coordination of 1 with Cu atom.
In the presence of the porous chiral metal-organic framework (2), enantioselective addition reaction of aniline to 1,2-epoxycyclohexane (3) proceeded in 51% ee to give an optically active aminolacohol (4) at room temperature. This is the first example for such a enantioselective reaction in chiral porous metal-organic framework.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (21 results)

All 2006 2005

All Journal Article (20 results) Book (1 results)

  • [Journal Article] Selective Inclusion of Equatrial Isomers of Cyclohexane-polyols with Phosphonium Salt Hosts2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Eur. J. Org. Chem.

      Pages: 2423-2428

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Optical Resolution of Medium-Size Lactones by Inclusion Crystallization with Optically Active Host Compounds2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Tetrahedron : Asymmetry 17

      Pages: 1678-1683

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Spontanious Resolution of 2, 3-Bisfluoren-9-ylidene Succinic Acid Induced by Achiral Guest Inclusion2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Chirality 18

      Pages: 483-488

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Resolution of 4-Oxazetidin-2-yl Benzoate by Inclusion Crystallization with Optically Active Host2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Tetrahedron : Asymmetry 17

      Pages: 2216-2219

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel Host Compounds, 1. 1'-Binaphthyl-2, 2'-dihydroxy-5, 5'- and -6, 6'-dicarboxylic Acid2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Journal of Inclusion Phenomena 56

      Pages: 281-285

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Guest Inclusion by N, N', N' '-Trihydroxyisocyanuric Acid2006

    • Author(s)
      M.R.Caira
    • Journal Title

      Analy. Sci. 22

      Pages: 69-70

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Selective Inclusion of Equatorial Isomers of Cyclohexane-polyols with Phosphonium Salt Hosts2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 2423-2428

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Optical Resolution of Medium-size Lactones by Inclusion Crystallization with Optically Active Host Compounds2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Tetrahedron : Asymmetry 17

      Pages: 1678-1683

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Spontaneous Resolution of 2,3-Bis-fluoren-9-ylidenesuccinic Acid Induced by Achiral Guest Inclusion2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Chirality 18

      Pages: 483-488

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Resolution of 4-oxazetidin-2-yl Benzoate by Inclusion Crystallization with an Optically Active Host Compound2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Tetrahedron : Asymmetry 17

      Pages: 2216-2219

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel Host Compounds, 1,1'-Binaphthy1-2,2'- dihydroxy-5,5'- and 6,6'-dicarboxylic acid2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Journal of Inclusion Phenomena 56

      Pages: 281-285

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Guest Inclusion by N,N',N"-Trihydroxyisocyanuric Acid2006

    • Author(s)
      M.R.Caira
    • Journal Title

      Anal.Sci. 22

      Pages: 69-70

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Selective Inclusion of Equatrial isomers of Cyclohexane-polyols with Phosphonium Salt Hosts2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 2423-2428

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Spotaneous Resolution of 2,3-bisfluoren-9-ylidene Succinic Acid Induced by Achiral Guest Inclusion2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Chirality 18

      Pages: 483-488

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Resolution of 4-Oxazetidin-2-yl enzoate by Inclusion Crystallization with Optically Active Host2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Tetrahedron : Asymmetry 17

      Pages: 2216-2219

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Novel Host Compounds,1,1'-binaphtyl-2,2'-dihydroxy-5,5'-and 6,6'-dicarboxylic acid2006

    • Author(s)
      K.Tanaka
    • Journal Title

      Journal of Inclusion Phenomena 56

      Pages: 281-285

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Solvent-Free Organic Synthesis2005

    • Author(s)
      K.Tanaka
    • Journal Title

      Kansai University, Kogakkai 13

      Pages: 1-71

    • NAID

      110004672721

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enantioselective [2+2]Photodimerization Reactions of Coumarins in Solution2005

    • Author(s)
      K.Tanaka, T.Fujiwara
    • Journal Title

      Organic Letters 7・8

      Pages: 1501-1503

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Photochromic Crystals : Toward an Understanding of Color Development in the Solid State2005

    • Author(s)
      J.L.Scott, K.Tanaka
    • Journal Title

      Crystal Growth & Design 5・3

      Pages: 1209-1213

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Solvent-mediated transformation of a 1:1 2,3-bis-fluoren-9-ylidene succinic acid-ethanol solvate to the 1:2 solvate2005

    • Author(s)
      K.Tanaka, S.Wada, M.R.Caira
    • Journal Title

      Cryst Eng Comm 7

      Pages: 592-594

    • Related Report
      2005 Annual Research Report
  • [Book] 無溶媒有機合成2005

    • Author(s)
      田中 耕一
    • Total Pages
      71
    • Publisher
      関西大学 工学会
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2005-04-01   Modified: 2016-04-21  

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