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Chiral Synthesis under Solvent-Free Conditions

Research Project

Project/Area Number 13640538
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionEhime University

Principal Investigator

TANAKA Koichi  Ehime Univ.Fac.of Eng., Associate Prof., 工学部, 助教授 (10116949)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2001: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordssolvent-free reaction / solid-state synthesis / photoreaction / chiral synthesis / Inclusion compound / host compound / tropolon ether / β-lactin / 光学活性ホスト / 包接結晶 / 固体光反応 / 酒石酸 / ロジン
Research Abstract

1. Synthesis of Optically Active Host Compounds
Novel optically active host compounds were synthesized from tartaric acid and abietic acid. For example, novel host compounds, 〔2-{4-〔4.5-bis-(hydroxydipheylmerbyl)-〔1.3〕dioxolan 2-yl〕-phenylz-5-(hydroxydiphenyluethyl)-〔1.3〕dioxolan-4-yl〕-diphynylmethaud(1) and (7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthreru-1-yl)-diphenylwethausl (2)were synthesized from tartaric acid and abietic acid, respectively.
2. Chiral Synthesis under Solvent-Free Conditions
Photoirradiation of the inclusion complex of optically active host compound and prochiral quest compound in the solid state gave optically active photoreaction products. For example, photoirradiation of the inclusion complex of optically active host and tropolone ether in the solid state gave optically active 7-methoxy-bicyclo〔3,2,0〕hepta-3.6-dieu-2-one in 48-96%ee. Similar photoirradiation of the inclusion complex of pyridone gave optically active 2-albyl-2-azabicyclo〔2,2,0〕hex-5-eu-3-one in 91-95%ee.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] K.Tanaka, F.Fujiwara, Z.Lipkowska: "Highly Enantioselective Photocyclization of 1-Alkyl-2-pyridone"Organic Letters. 4. 3255-3257 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, R.Nagahiro, Z.Lipkowska: "Enantioselective Photoreaction of Achiral Tropolone Ether"Chirality. 14. 568-572 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, N.Harada: "A Novel Spiroketalization of 1,7-Dihydroxyhepta-2,5-diyu-4-ones"J. Chem. Soc., Perkin Troms. 1. 713-714 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, M.Asami, J.L.Scot: "A Novel Chromogenic Host Compound"New Journal of Chemistry. 26. 378-380 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, T.Hiratsuka, Y.Kojima, Y.T.Osano: "Synthesis, Structure and Chiral Inclusion Crystallization"J. Chem. Research (s). 209-212 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, N.Daikawa, S.Ohba: "Novel Bisurea Host Compounds"J. Chem. Research (s). 579-581 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka: "Solvent-Free Organic Synthesis"Weily-VCH. 433 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, T.Fujiwara, Z.Lipkowska: "Highly Enantioselective photoreaction of 1-Alkyl-2-pyridones to β-lactains in indusion crystals"Org.Lett.. 4. 3255-3257 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, R.Nagahiro, Z.Lipkowska: "Enantioseletive photoreaction of Aciral Tropdone Ether in Inclusion Crystals with Optically Active Host Compound"Chirality. 14. 568-572 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, N.Harada: "A Novel Spiroketalization of 1,7-Dihydroxy-hepta-2,5-diyn-4-ones"J.Chem.Soc., Perkin Trans 1. 713-714 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, M.Asami, J.L.Scott: "A Novel Chromogenic Host Compound"New Journal of Chemistry. 26. 378-380 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, T.Hiratsuka, Y.Kojima, Y.T.Osano: "Synthesis, Structure and Chiral Inclusion Crystallization"J.Chem.Res(S). 209-212 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka, N.Daikawa, S.Ohba: "Novel Bisurea Host Compounds"J.Chem.Res(S). 579-581 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Tanaka: "Solvent-Free Organic Synthesis"Weily-VCH. 433 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] k.Tanaka, T.Fujiwara, Z.Lipkowska: "Highly enantioselective Photocyclization of 1-Alkyl-2-pyridones to β-Lactams in Inclusion Crystals with Optically Active Host Compounds"Organic Letters. 4・19. 3255-3257 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, R.Nagahiro, Z.Lipkowska: "Enantioselective Photoreaction of Achiral Tropolone Ether in Inclusion Crstals with Optically Active Host Compounds"Chirality. 14. 568-572 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, N.Harada: "A Novel Spiroketalization Reaction of 1,7-Dihydroxyhepta-2,5-diyn-4-ones"J. Chem. Soc., Perkin Trans. 1. 713-714 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, M.Asami, J.L.Scott: "A Novel Chromogenic Host Compound that Shows Sensitive Color Change upon Inclusion Crystallization"New Journal of Chemistry. 26. 378-380 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, T.Hiratsuka, Y.Kojima: "Synthesis, structure and chiral inclusion crystallization of tetrakis(4-ethynylphenyl)ethylene derivatives"J. Chem. Research(S). 5. 209-212 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, N.Daikawa, S.Ohba: "Novel Bisurea Host Compounds"J. Chem. Research(S). 11. 579-581 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Koichi Tanaka: "Solvent-Free Organic Synthesis"Weily-VCH. 433 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Tanaka, R.Nagahiro, Z.Lipkowska: "Erantioselective Photoreaction of 4-Isopropyl tropolone Methyl Ether in Iocution Crystals with Optically Active Host Compounds"Org. Lett.. 3・10. 1567-1569 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Tanaka, R.Nagahiro, Z.Lipkowska: "Erantioselective Photoreaction of Achiral Tropolone Ether in Inclusion Crystals with Optically Active Host Compounds"Chirality. (印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Tanaka, N.Harada: "A Novel Spivoketalization of 1.7-D-hydroxy-hepta-2.5-diyn-4-ones"J. Chem. Soc., Perkin Trans 1. (印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Tanaka, M.Asami, J.L.Scott: "A Novel Chromogenic Host Compound which shows sensitive color change upon Inclusion Crystallization"New. J. Chem.. (印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Tanaka, T.Fukuoka, M.Shiro: "Optical Resolution of Maudelic Acid by Complexation with (s)-(t)-Alanine"J. Chem. Res (S). (印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Tanaka, T.Horino, M.Shiro: "Synthesis and Inclusion Properties of Novel Host Compounds Derived from Abietic Acid"J. Chem. Res (S). 17-19 (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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