• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

The Synthesis of enantiomerically pure novel liquid crystal compounds containing the bis(trifluoromethyl)alkanediol moiety.

Research Project

Project/Area Number 16550125
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionKagawa University

Principal Investigator

TAKAGI Yumiko  Kagawa University, Faculty of Education, Assistant Professor, 教育学部, 助教授 (50263413)

Co-Investigator(Kenkyū-buntansha) NISHIHARA Hiroshi  Kagawa University, Faculty of Education, Professor, 教育学部, 教授 (80036029)
ITOH Toshiyuki  Tottori University, Faculty of Engineering, Professor, 工学部, 教授 (50193503)
Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsFerroelectric liquid crystal compounds / Anti-ferroelectric liquid crystal compounds / Lipase / Fluoro Alkanol / Optically Pure
Research Abstract

Ant ferroelectric liquid crystal compounds(AFCLs), which possess a chiral 1,1,1-trifluoromethyl-2-alkanol moiety, are known to be important high-speed switching devices. Kusumoto and his colleagues recently the synthesis of unique dimeric AFLCs molecules which contain optically active bis(trifluoromethyl)alkanediols as chiral core units. The reported means for preparing optically pure bis(trifluoromethyl)alkanediols, however, required a nuisance resolution process using HPLC on chiral phase. We previously reported that Candida antarctica lipase catalyzed trans-esterification of racemic 1,1,1-trifluoro-2-alkanols with perfect enantioselectivity. We also achieved the hydrolysis of acetate more effectively. We next attempted trans-sterification of diol 1 in organic solvent using vinyl acetate as an acyl donor. Trans-esterification, however, did not take place. Fortunately, hydrolysis reaction of (±)-1 proceeded smoothly to provide monoacetate and diol with efficient enantioselectivity. We report the results of lipase-catalyzed hydrolysis reaction of bis(trifluoromethyl)alkanediols. Using optically active bis(trifluormethyl)-alkanediols obtained in this reaction as starting materials, synthesis of novel dimer type AFCLs has been demonstrated.

Report

(4 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (51 results)

All 2007 2006 2005 2004 Other

All Journal Article (37 results) Book (11 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Alkylation of N-protecting group free indole with vinyl ketones using iron salt catalyst2007

    • Author(s)
      Itoh, T., Uehara, H., Ogiso, K., Nomura, S., Hayase, S., Kawatsura, M.
    • Journal Title

      Chemistry Letters 36・1

      Pages: 50-51

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Ruthenium-catalysed linear-selective allylic alkylation of allyl acetates2007

    • Author(s)
      Kawatsura, M., Ata, F., Wada, S., Hayase, S., Uno, H., Itoh, T.
    • Journal Title

      Chemical Communications

      Pages: 298-300

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Gem-Difluorocyclopropane as Core Molecule Candidate for Liquid Crystal Compounds2007

    • Author(s)
      Itoh, T., Kanbara, M., Ohashi, M., Hayase, S., Kawatsura, M., Kato T., Miyazawa, K., Takagi, Y., Uno, H.
    • Journal Title

      J. Fluorine. Chem (inpress)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] イオン液体中の酵素反応2007

    • Author(s)
      伊藤敏幸
    • Journal Title

      現代化学 No432・3

      Pages: 28-32

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Alkylation of N-Protecting Group-free Indole with Vinyl Ketones Using Iron Salt Catalyst2007

    • Author(s)
      Itoh, T., Uehara, H., Ogiso, K., Nomura, S., Hayase, S., Kawatsura, M
    • Journal Title

      Chem. Lett 36

      Pages: 50-51

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Ruthenium-catalysed linear-selective allylic allylation of allyl acetates2007

    • Author(s)
      Kawatsura, M., Ata, F., Wada, S., Hayase, S., Uno, H., Itoh, T.
    • Journal Title

      Chemical Communications

      Pages: 298-300

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Gem-Difluorocyclopropane as Core Molecule Candidate for Liquid Crystal Compounds2007

    • Author(s)
      Itoh, T., Kanbara, M., Ohashi, M., Hayase, S., Kawatsura, M., Kato, T., Miyazawa, K., Takagi, Y., Uno, H.
    • Journal Title

      J.Fluorine.Chem (inpress)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enzymatic reaction using Ionic Liquid.2007

    • Author(s)
      Itoh Toshiyuki
    • Journal Title

      Modern chemistry 432(3)

      Pages: 28-32

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Alkylation of N-protecting Group-free Indole with Vinyl Ketones using Iron Salt Catalyst2007

    • Author(s)
      Itoh, T;, Uehara, H;, Ogiso, K;, Nomura, S;, Hayase, S;, Kawatsura, M
    • Journal Title

      Chem.Lett 36

      Pages: 50-51

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Biotransformation in ionic liquid2007

    • Author(s)
      Toshiyuki Itoh
    • Journal Title

      Future Directions in Biocatalysis ( Ed. T.Matsuda a Elsevier Bioscience The Netherlands) (In press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Gem-Difluorocyclopropane as Core Molecule Candidate for Liquid Crystal Compounds,2007

    • Author(s)
      Itoh, T;, Kanbara, M;, Ohashi, M;, Hayase, S;, Kawatsura, M;, Kato, T;, Miyazawa, K;, Takagi, Y;, Uno, H.
    • Journal Title

      J.Fluorine.Chem (In press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Preparation of Novel Hydrophobic Fluorine-substituted-alkyl sulfate Ionic Liquids and Application as an Efficient Reaction Medium for Lipase-catalyzed Reaction2006

    • Author(s)
      Tsukada, Yasuhiro, Iwamoto, Kazuhisa, Furutani, Hiroyuki, Matsushita, Yuichi, Abe, Yoshikazu, Matsumoto, Kei, Monda, Keishi, Hayase, Shuichi, Kawatsura, Motoi, Itoh, Toshiyuki
    • Journal Title

      Tetrahedron Letters 48

      Pages: 1801-1804

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] A novel 1,4-addition type reaction of β-keto esters with vinyl ketones catalyzed by iron(II)tetrafluoroborate in an ionic liquid solvent system2006

    • Author(s)
      Uehara, H., Nomura, S., Hayase, S., Kawatsura, M., Itoh, T.
    • Journal Title

      Electrochemistry 74・8

      Pages: 635-638

    • NAID

      10017390086

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel gem-difluorinatedcyclopropane hybrids : applications for DNA cleavage agents switched by photo irradiation2006

    • Author(s)
      Ninomiya, Keiko, Tanimoto, Kunihiko, Ishida, Nanae, Horiii, Daisuke, Sisido Masahiko, Itoh, Toshiyuki
    • Journal Title

      J. Fluorine Chem

      Pages: 651-656

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Palladium-catalyzed regioselective allylic alkylation of 1-aryl-2,3,3-trifluoroallyl acetates2006

    • Author(s)
      Kawatsura, M., Wada, S., Hayase, S., Itoh, T.
    • Journal Title

      SYNLETT

      Pages: 2483-2485

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enhanced enantioselectivity and remarkable acceleration of lipase-aatalyzed transesterification using an Imizadolium PEG-alkyl sulfate ionic liquid2006

    • Author(s)
      Itoh, T., Matsushita, Y, Abe, Y., Han, S-H., Wada, S., Hayase, S., Kawatsura, M., Takai, S., Morimoto, M., Hirose, Y.
    • Journal Title

      Chemistry-A European Journal 12

      Pages: 9228-9237

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A novel 1,4-addition type reaction of b-keto esters with vinyl ketones catalyzed by iron(II)tetrafluoroborate in an ionic liquid solvent system2006

    • Author(s)
      Uehara, H., Nomura, S., Hayase, S., Kawatsura, M., Itoh, T
    • Journal Title

      Electrochemistry 74

      Pages: 635-638

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel gem-difluorinatedcyclopropane hybrids : applications for DNA cleavage agents switched by photo irradiation2006

    • Author(s)
      Ninomiya, Keiko, Tanimoto, Kunihiko, Ishida, Nanae, Horiii, Daisuke, Sisido Masahiko, Itoh, Toshiyuki
    • Journal Title

      J.Fluorine Chem 127

      Pages: 651-656

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enhanced enantioselectivity and remarkable acceleration of lipase-aatalyzed transesterification using an Imizadolium PEG-alkyl sulfate ionic liquid2006

    • Author(s)
      Kawatsura, M., Wada, S., Hayase, S., Itoh, T
    • Journal Title

      Synlett.

      Pages: 2483-2485

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Novel 1,4-Addition Type Reaction of β-Keto Esters with Vinyl Ketones Catalyzed by Iron(II)tetrafluoroborate in an Ionic Liquid Solvent System2006

    • Author(s)
      Itoh, T., Matsushita, Y., Abe, Y., Han, S-H., Wada, S., Hayase, S., Kawatsura, M., Takai, S., Morimoto, M., Hirose, Y.
    • Journal Title

      Chemistry-A European Journal 12

      Pages: 9228-9237

    • NAID

      10017390086

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Novel 1,4-Addition Type Reaction of b-Keto Esters with Vinyl Ketones Catalyzed by Iron (II) tetrafluoroborate in an Ionic Liquid Solvent System2006

    • Author(s)
      Uehara, Hiroyuki, Nomura, Shun, Hayase, Shuichi, Kawatsura, Motoi, Itoh, Toshiyuki
    • Journal Title

      Electrochemistry (in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of novel gem-difluorinatedcyclopropane hybrids: applications for DNA cleavage agents switched by photo irradiation2006

    • Author(s)
      Ninomiya, Keiko, Tanimoto, Kunihiko, Ishida, Nanae, Horiii, Daisuke, Sisido Masahiko, Itoh, Toshiyuki
    • Journal Title

      J Fluorine Chem 127(in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Novel alkylation of indole and pyrrole derivatives using Iron (II) tetrafluoroborate as a catalyst in an ionic liquid solvent2006

    • Author(s)
      Itoh, Toshiyuki
    • Journal Title

      Abstracts of Papers, 231st ACS National Meeting, Atlanta, GA, Unit ed States, March 26-30, 2006

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Enhanced enantioselectivity and stabilization of an enzyme using novel ionic liquids2005

    • Author(s)
      Itoh, T., Han, S., Matsushita, Y., Wada, S., Hayase, S., Hayase, S., Ohara, H., Oyama, M.
    • Journal Title

      Separation and Purification Technology 41(In press)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of novel liquid crystal compounds which have bis(trifluoromethyl)alkanediol moiety in optically pure form2004

    • Author(s)
      Takagi, Y., Yamana, F., Sumino, F., Ito, H., Yoshida, T., Kato, T., Miyazawa, K., Itoh, T.
    • Journal Title

      Tetrahedron; Asymmetry 15

      Pages: 2591-2594

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of Optically Active gem-Difluorocyclopropanes through a Chemo-Enzymatic Reaction Strategy2004

    • Author(s)
      Itoh, T., Ishida, N., Mitsukura, K., Hayase, S., Ohashi, K.
    • Journal Title

      J. Fluorine Chem 125

      Pages: 775-783

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration on the Lipase-Catalyzed Transeste rification Using Novel Ionic Liquids2004

    • Author(s)
      Itoh, T., Han, S., Matsushita, Y., Hayase, S.
    • Journal Title

      Green Chemistry 6・9

      Pages: 437-439

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ヘッドライン 注目される新しい化学反応場,反応媒体"テーラメイドなイオン性液体を反応媒体とする酵素反応"2004

    • Author(s)
      伊藤敏幸
    • Journal Title

      化学と教育 52・8

      Pages: 520-523

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2004 Annual Research Report
  • [Journal Article] イオン性液体中の酵素反応2004

    • Author(s)
      伊藤敏幸
    • Journal Title

      機能材料 24・11

      Pages: 27-33

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2004 Annual Research Report
  • [Journal Article] The Synthesis of enantiomerically pure novel liquid crystal compounds containing the bis(trifluoromethyl)alkanediol moiety.2004

    • Author(s)
      Takagi, Y, Yamana, F., Sumino, F., Ito, H., Yoshida, T., Kato, T., Miyazawa, K., Itoh, T.
    • Journal Title

      Tetrahedron ; Asymmetry 15

      Pages: 2591-2594

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of Optically Active gem-Difluorocyclopropanes through a Chemo-Enzymatic Reaction Strategy2004

    • Author(s)
      Itoh, T., Ishida, N., Mitsukura, K., Hayase, S., Ohashi, K.
    • Journal Title

      J.Fluorine Chem 125

      Pages: 775-783

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary 2004 Annual Research Report
  • [Journal Article] Hayase, Enhanced Enantioselectivity and Remarkable Acceleration on the Lipase-Catalyzed Transesterification Using Novel Ionic Liquids2004

    • Author(s)
      Itoh, T., Han, S., Matsushita, Y.
    • Journal Title

      Green Chemistry 6-9

      Pages: 437-439

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enzymatic Reaction using Ionic Liquids as a tailor-made solvent.2004

    • Author(s)
      Itoh, T.
    • Journal Title

      Chemical Fducation Japan 52

      Pages: 520-528

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Enzymatic Reaction using Ionic Liquids2004

    • Author(s)
      Itoh, T.
    • Journal Title

      Functional materials 24

      Pages: 24-33

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of novel liquid crystal compounds which have bis(trifluoromethyl)alkanediol moiety in optically pure form2004

    • Author(s)
      Takagi, Y., Yamaha, F., Sumino, F., Ito, H., Yoshida, T., Kato, T., Miyazawa, K., Itoh, T.
    • Journal Title

      Tetrahedron ; Asymmetry 15

      Pages: 2591-2594

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Enhanced Enantioselectivity and Remarkable Acceleration on the Lipase-Catalyzed Transesterification Using Novel Ionic Liquids2004

    • Author(s)
      Itoh, T., Han, S., Matsushita, Y., Hayase, S.
    • Journal Title

      Green Chemistry 6・9

      Pages: 437-439

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A Novel 1,4-Addition Type Reaction of b-Keto Esters with vinyl Ketones Catalyzed by Iron(II)tetrafluoroborate in an Ionic Liquid Solvent System

    • Author(s)
      Uehara, Hiroyuki;, Nomura, Shun;, Hayase, Shuichi;, Kawatsura, Motoi;, Itoh, Toshiyuki
    • Journal Title

      Electrochemistry 7

      Pages: 635-638

    • Related Report
      2006 Annual Research Report
  • [Book] イオン液体と触媒2007

    • Author(s)
      伊藤敏幸
    • Publisher
      触媒(In press)
    • Related Report
      2006 Annual Research Report
  • [Book] イオン液体中の酵素反応2007

    • Author(s)
      伊藤敏幸
    • Publisher
      現代化学(In press)
    • Related Report
      2006 Annual Research Report
  • [Book] イオン液体を反応媒体に用いる酵素触媒反応 酵素開発・利用の最新技術,第4編第1章(監修 : 今中忠行)2006

    • Author(s)
      伊藤敏幸
    • Total Pages
      309
    • Publisher
      CMC出版
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] イオン液体II-驚異的な進歩と多彩な近未来-「イオン液体を反応媒体に用いるリパーゼ触媒反応」(大野弘幸編)2006

    • Author(s)
      伊藤敏幸
    • Total Pages
      299
    • Publisher
      CMC出版
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] 「イオン液体を反応媒体に用いる酵素触媒反応」酵素開発・利用の最新技術酵素 開発・利用の最新技術(監修:今中忠行)4編1章2006

    • Author(s)
      伊藤敏幸
    • Publisher
      CMC出版
    • Related Report
      2006 Annual Research Report
  • [Book] イオン液体II-驚異的な進歩と多彩な近未来-,大野弘幸編,東京2006

    • Author(s)
      伊藤敏幸
    • Publisher
      CMC出版
    • Related Report
      2005 Annual Research Report
  • [Book] Optically Active gem-Difluorocyclopropanes; Synthesis and Application for Novel Molecular Materials, ACS Symposium Series #9112005

    • Author(s)
      Itoh, T.
    • Publisher
      Oxford University Press/ American Chemical Society : Washington DC
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] "Fluorine-Containing Synthons," ACS Symposium Series #911, Ed, V. A. Soloshonok2005

    • Author(s)
      Itoh, Toshiyuki
    • Publisher
      Oxford University Press/ American Chemical Society: Washington DC
    • Related Report
      2005 Annual Research Report
  • [Book] Optically_Active gem-Difluorocyclopropanes, Synthesis and Application for Novel Molecular Materials, ACS Symposium Series #9112005

    • Author(s)
      Itoh, T.
    • Publisher
      Oxford University Press/ American Chemical Society : Washington DC
    • Related Report
      2004 Annual Research Report
  • [Book] Analytical Mechanistic and Synthetic Organic Electrochemistry-6th International M. Baizer Award Symposium in Honor of Dennis H. Evans and Masao Tokuda2004

    • Author(s)
      Itoh, T., Uehara, H., Kawai, K., Hayase, S., Ohara, H., Oyama, M.
    • Publisher
      The Electrochemical Society, Inc. USA
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] Analytical Mechanistic and Synthetic Organic Electrochemistry- 6th International M.Baizer Award Symposium in Honor of Dennis H.Evans and Masao Tokuda2004

    • Author(s)
      Itoh, T., Uehara, H., Kawai, K., Hayase, S., Ohara, H., Oyama, M.
    • Publisher
      The Electrochemical Society, Inc.USA
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] ポイントジフルオロ化イオン液体2006

    • Inventor(s)
      伊藤敏幸, 古谷浩行, 塚田泰弘
    • Industrial Property Rights Holder
      鳥取大学
    • Industrial Property Number
      2006-014677
    • Filing Date
      2006-01-25
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Patent(Industrial Property Rights)] 磁性を有するフラーレン誘導体2006

    • Inventor(s)
      伊藤敏幸, 古谷浩行
    • Industrial Property Rights Holder
      鳥取大学, 株式会社カネカ
    • Industrial Property Number
      2006-119762
    • Filing Date
      2006-04-24
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 磁性を有するフラーレン誘導体2006

    • Inventor(s)
      伊藤敏幸, 古谷浩行
    • Industrial Property Rights Holder
      鳥取大学長 能勢隆之
    • Filing Date
      2006-04-24
    • Related Report
      2006 Annual Research Report

URL: 

Published: 2004-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi