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

Enantioresolution of Alcohols and its Application to Organic Synthesis

Research Project

Project/Area Number 14540552
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 分離・精製・検出法
Research InstitutionTohoku University

Principal Investigator

WATANABE Masataka  Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Associate Professor, 多元物資科学研究所, 助教授 (10006330)

Co-Investigator(Kenkyū-buntansha) KUWAHARA Shunsuke  Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Research Associate, 多元物資科学研究所, 助手 (40359550)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2003: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
Keywords(S)-(+)-MαNP Acid / aryl methanol / diary methanol / 4-butylphthalide / matsutakeol / alcohols with aliphatic long-chain / enantioresolution / asymmetric synthesis / MαNP Acid / 光学活性 / Phthalide / キラル源 / ジオール類 / 長鎖不飽和アルコール類 / プロパキルアルコール / (S)-Caminoside / NαNPA / CSPPA / 絶対配置 / 二級アルコール / 3-ブチルフタライド / 3-アルキルフタライド / エナンチオマー / ジフェニルメタノール類 / キラルフタル酸 / MαNP酸 / 絶対立体化学 / 含フッ素ジフェニルメタノール酸 / 計算機化学 / 光学分割のメカニズム
Research Abstract

(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic acid so-called (S)-(+)-MαNP Acid, which was devised together by Professor Nobuyuki Harada, Dr shunsike Kuwahara and myself, has two roles ; one is diastereomeric separation of secondary alcohols and the other is simultaneous determination of absolute configuration of the hydroxyl group of the alcohols. We have paid our attention to these roles of our new chiral auxiliary, and reported syntheses of variety kinds of optical active aryl methanol and diary methanol, using the chiral auxiliary. We also focused on 4-butylphthalide known as a major fragrance of celery oil determined whose research started in 1890's. The absolute configuration of 4-butylphthalide has been speculated by the mechanism of asymmetric synthesis. The structure of the fragrance was finally determined as (S)-(-)-4-butylphthalide. We also succeeded in the synthesis of two enantiomers of the fragrance of matsutake mushroom known as "matsutakeol".
It is well known that enantioresolution of alcohols with aliphatic long-chaine and the determination of absolute configuration of the hydroxyl groups is difficult. There has been also no report of asymmetric synthesis of such alcohols. We, recently, succeeded in the enantioresolution of such alcohols with 36 carbons prepared from oleic acid and determination of absolute configuration of its hydroxyl group. This is a promising methodology to synthesis of biological active alcohols consists of long-chain aliphatic substituents.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (60 results)

All 2005 2004 2003 2002 Other

All Journal Article (44 results) Book (3 results) Patent(Industrial Property Rights) (1 results) Publications (12 results)

  • [Journal Article] Enantiosepartion Separation of a Powerfrl Chiral Auxiliary, 2-methoxy-2-(1-naphthyl propionic Acid by Liquid Chromatography Using Chiral Anion Exchanger Type Stationary Pahses in Polar-Organic Mode; Investigation of Molecular Recognition Aspects.2005

    • Author(s)
      Krisztina Gyimesi-Forras
    • Journal Title

      Chirality. 17

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Enantiopure Phthalides Including 3-Butylphthalide, a Fragrance Component of Celery Oil, and Determination of Their Absolute Configurations.2005

    • Author(s)
      Masashi Kosaka
    • Journal Title

      Chirality. 17

      Pages: 218-232

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Snthesis and Dynamic Stereochemistry of Azulene-Substitutted 9-Fluorenyl,9,10-Dihydro-10,10-dimethyl-9-anthryl, 10,11-Dihydor-5H0dibenzo[a,d]cyclohepten-5-yl, and 5H-Dibenzo[a,d]cyclohepten-5-yl Cations. Correlations of Stabilities of the Carbocations and Rotational Barrier of Azulene Ring.2005

    • Author(s)
      Shunji Ito
    • Journal Title

      Bulletin of the Chemical Society of Japan. 78

      Pages: 2051-2065

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Unambiguous Determination of the Absolute Configurations of Acetylenic Alcohols by Combination of the Sonogashira Reaction and the Cd Exiton Chirality Method-Exciton Coupling between Phenylacetylene and Benzoate Chromophores.2005

    • Author(s)
      Junpei Naito
    • Journal Title

      Monatshefte fur Chemie Chemical Monthly. 136

      Pages: 411-445

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Preparation of Enantiopure Wieland-Miescher Ketone and Derivatives by the MαNP Acid Method. Substituent Effect on the HPLC Separation.2005

    • Author(s)
      Yusuka Kasai
    • Journal Title

      Chiralith. 18(in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Enantioseparation Separation of a Powerful Chiral Auxiliary, 2-methoxy-2-(1-naphthyl) propionic Acid by Liquid Chromatography Using Chiral Anion Exchanger Type Stationary Phases in Polar-Organic Mode ; Investigation of Molecular Recognition Aspects.2005

    • Author(s)
      Krisztina Cyimesi-Forras.
    • Journal Title

      Chirality 17

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Enantiopure Phthalides Including 3-Butylphthalide, a Fragrance Component of Celery Oil, and Determination of Their Absolute Confiturations.2005

    • Author(s)
      Masashi Kosaka.
    • Journal Title

      Chirality 17

      Pages: 218-232

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Snthesis and Dynamic stereochemistry of Azulene-Substitutted 9-Fluorenyl,9,10-Dihydro-10,10-dimethyl-9-anthryl,10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl, and 5H-Dibenzo[a,d]cyclohepten-5-yl Cations. Correlations of Stabilities of the Carbocations and Rotational Barrier of Azulene Ring.2005

    • Author(s)
      Shunji Ito.
    • Journal Title

      Bulletin of the Chemical Society of Japan 78

      Pages: 2051-2065

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Unambiguous Determination of the Absolute Configurations of Acetylenic Alcohols by Combination of the Sonogashira Reaction and the CD Exiton Chirality Method-Exciton Coupling between Phenylacetylene and Benzoate Chromophores.2005

    • Author(s)
      Junpei Naito.
    • Journal Title

      Monatshefte fur Chemie Chemical Monthly 136

      Pages: 411-445

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Preparation of Enantiopure Wieland-Miedscher Ketone and Derivatives by the MaNP Acid Method. Substituent Effect on the HPLC Separation.2005

    • Author(s)
      Yusuke Kasai.
    • Journal Title

      Chirality 18(in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Unambiguous Determination of the Absolnute Configurations of Acetylene Alcohols by Combination of the Sonogashira Reactions and the CD Exiciton Chirality Method-Exiciton Coupling between Phenylacetylene and Benzoate Chromophores2005

    • Author(s)
      Junpei Naito
    • Journal Title

      Monatshefte 2005(印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Enantioresolution of Fluorinated Diphenylmethanols and Deteermination of Their Absolute Configurations by X-ray Crystallographic ^1H NMR Anisotropy Methods.2004

    • Author(s)
      Junpei Naito
    • Journal Title

      Chirality. 16

      Pages: 22-35

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] M aNP Acid, a Powerful Chiral Molecular Tool for Preparation of Enantiopure Alcohols by Resolution and Determination of Their Absolute Configurations by the ^1H NMR Anisotropy Method.2004

    • Author(s)
      Yusuke Kasai
    • Journal Title

      Chirality, 16,569-585(2004). 16

      Pages: 569-585

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Investigations of Molecular Recognition Aspects Related to the Enantiomer Separation of 2-methoxy-2-(1-naphthyl)propionic Acid Using Qunine Carbamate as Chiral Selector An NMR and FT-IR Spectroscopic as Well as X-Ray Crystllographic Study.2004

    • Author(s)
      kazuaki Akasaka
    • Journal Title

      Chirality. 17

      Pages: 544-555

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] The effect of aromatic substituents on the chromatographic enantioseparation of diarylesters with Whelk-Ol chiral stationary phase.2004

    • Author(s)
      Gabriel E. Job
    • Journal Title

      Journal of Chromatography A. 1055

      Pages: 41-53

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Enantioresolution of Fluorinated Diphenylmethanols and Determination of Their Absolute Configurations by X-ray Crystallographic and ^1H NMR Anisotropy Methods.2004

    • Author(s)
      Junpei Naito.
    • Journal Title

      Chirality 16

      Pages: 22-35

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] MαNP Acid, a Powerful Chiral Molecular Tool for Preparation of Enantiopure Alcohols by Resolution and Determination of Their Absolute Configurations by the 1H NMR Anisotropy Method.2004

    • Author(s)
      Yusuke Kasai.
    • Journal Title

      Chirality 16

      Pages: 569-585

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Investigations of Molecular Recognition Aspects Related to the Enantiomer Separation of 2-methoxy-2-(1-naphthyl)propionic Acid Using Qunine Carbamate as Chiral Selector : An NMR and FT-IR Spectroscopic as Well as X-Ray Crystllographic Study.2004

    • Author(s)
      Kazuaki Akasaka.
    • Journal Title

      Chirality 17

      Pages: 544-555

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] The effect of aromatic substituents on the chromatographic enantioseparation of diaryl esters with Whelk-O1 chiral stationary phase.2004

    • Author(s)
      Gabriel E.Job.
    • Journal Title

      Journal of Chromatography A 1055

      Pages: 41-53

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Enantioresolution of Fluorinated Diphenyl Methanols and Determination of Their Configuration by X-Ray Crystallographic and ^1H NMR Anisotropy Methods.2004

    • Author(s)
      Junpei Naito
    • Journal Title

      Chirality 16

      Pages: 22-35

    • Related Report
      2004 Annual Research Report
  • [Journal Article] MαNP Acid, a Powerful Chiral Molecular Tool for Preparation of Enantiopure Alcohols by Resolution and Determination of Their Absolute Configuration by the ^1H NMR Anisotropy Method.2004

    • Author(s)
      Yusuke Kasai
    • Journal Title

      Chirality 16

      Pages: 569-585

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Enantioseparation of a Powerful Chiral Auxiliary, 2-methoxy-2-(1-naphthyl)propionic Acid by Liquid Chromatography Using Chiral Anion Exchanging Type Stationary Phases in Polar-Organic Mode ; Investigation of Molecular Recognition Aspect.2004

    • Author(s)
      Krisztina G-Forras
    • Journal Title

      Chirality 16(印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Enantioseparation of a Powerful Chiral Auxiliary, 2-methoxy-2-(1-naphthyl)propionic Acid by Liquid Chromatography Using Chiral Anion Exchanging Type Stationary Phases in Polar-Organic Mode ; Investigation of Molecular Recognition Aspect II.2004

    • Author(s)
      Kazuaki Akasaka
    • Journal Title

      Chirality 16(印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of Enantiopure Phthalides Including 3-Butylphthalide, a Fragrance Component Celery Oil, and Determination of Their Configuration.2004

    • Author(s)
      Masashi Kosaka
    • Journal Title

      Chirality 16(印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Convenient Method for Determining the Absolute Configuration of Chiral Alcohols with Racemic ^1H NMR Anisotropy Reagent, MaNP Acid. Use of HPLC-CD Detector.2003

    • Author(s)
      Yusuke Kasai
    • Journal Title

      Chirality. 15

      Pages: 295-299

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Enantioresolution and Absolute Configurations of Chiral meta-Substituted Diphenylmethanols as Determined by the X-ray Crystallographic and ^1H NMR Anisotropy Methods.2003

    • Author(s)
      Masashi Kosaka
    • Journal Title

      Chiralith. 15

      Pages: 324-328

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis, stability and bonding situation of tris-, bis- and mono[9-(azuleno[1,2-b]thienyl)] methyl cations.2003

    • Author(s)
      Shunji Ito
    • Journal Title

      Organic and Biomolecular Chemistry. 1

      Pages: 2572-2580

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Convenient Method for Determining the Absolute Configuration of Chiral Alcohols with Racemic ^1H NMR Anisotropy Reagent, MαNP Acid. Use of HPLC-CD Detector.2003

    • Author(s)
      Yusuke Kasai.
    • Journal Title

      Chirality 15

      Pages: 295-299

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Enantioresolution and Absolute Configurations of Chiral meta-Substituted Diphenylmethanols as Determined by the X-ray Crystallographic and ^1H NMR Anisotropy Methods.2003

    • Author(s)
      Masashi Kosaka.
    • Journal Title

      Chirality 15

      Pages: 324-328

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis, stability and bonding situation of tris-, bis- and mono[9-(azuleno[1,2-b]thienyl)]methyl cations.2003

    • Author(s)
      Shunji Ito.
    • Journal Title

      Organic and Biomolecular Chemistry 1

      Pages: 2572-2580

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Practical Enantioresolution of Alcohols with 2-Methoxy-2-(1-naphthyl)propionic acid and Determination of Their Absolute Configurations by the ^1H・NMR Anisotropy Method.2002

    • Author(s)
      Hiromi Taji
    • Journal Title

      Chirality. 14

      Pages: 81-84

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Comparison of CD Spectra of (2-Methylphenyl)-and(2,6-Dimethylphenyl)-phenylmethanols Leads to Erroneous Absolute Configuration.2002

    • Author(s)
      Masashi Kosaka
    • Journal Title

      Enantiomer. 6

      Pages: 213-217

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Crystalline State Conformation of 2-Methoxy-2-(1-naphthyl)propionic Acid Ester.2002

    • Author(s)
      Takuma Fujita
    • Journal Title

      Enantiomer. 6

      Pages: 219-223

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A boslute Stereochemistry of Chiral C60 Fullerene Bis-Adducts.2002

    • Author(s)
      Kazuhiro Yoshida
    • Journal Title

      Enantiomer. 7

      Pages: 23-32

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Reaction of (η^4-cycloheptatriene)Fe(CO)^3 with haloketones : structure and reactivity of the cycloadducts.2002

    • Author(s)
      Shinji Ito
    • Journal Title

      Journal of Organometallic Chemistry. 648

      Pages: 164-175

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereomer Method for Determining %EE by ^1H NMR and/or MS Spectrometry with Complete Removal of the Kinetic Resolution Effect.2002

    • Author(s)
      Hiromi Taji
    • Journal Title

      Organic Letters. 4

      Pages: 2699-2702

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Absolute Configuration of 2-Methoxy-2-(1-naphthyl)propionic and 2-Methoxy-2-(2-naphthyl)propionic Acids as Determined by the Phenylglycine Methyl Ester(PGME) Method.2002

    • Author(s)
      Akio Ichikawa
    • Journal Title

      Tetrahedron : Asymmetry. 13

      Pages: 1167-1172

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Practical Enantioresolution of Alcohols with 2-methoxy-2-(1-naphthyl)propionic acid and Determination of Their Absolute Configurations by the ^1H NMR Anisotropy Method2002

    • Author(s)
      Hiromi Taji.
    • Journal Title

      Chirality 14

      Pages: 81-84

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Comparison of CD Spectra of (2-Methylphenyl)- and (2,6-Dimethylphenyl)-phenylmethanols Leads to Erroneous Absolute Configuration.2002

    • Author(s)
      Masashi Kosaka.
    • Journal Title

      Enantiomer 6

      Pages: 213-217

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Crystalline State Conformation of 2-Methoxy-2-(1-naphthyl)propionic Acid Ester.2002

    • Author(s)
      Takuma Fujita.
    • Journal Title

      Enantiomer 6

      Pages: 219-223

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Absolute Stereochemistry of Chiral C60 Fullerene Bis-Adducts.2002

    • Author(s)
      Kazuhiro Yoshida.
    • Journal Title

      Enantiomer 7

      Pages: 23-32

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Reaction of (η4-cycloheptatriene)Fe(CO)^3 with haloketones : structure and reactivity of the cycloadducts.2002

    • Author(s)
      Shunji Ito.
    • Journal Title

      Journal of Organometallic Chemistry 648

      Pages: 164-175

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereomer Method for Determining % EE by ^1H NMR and/or MS Spectrometry with Complete Removal of the Kinetic Resolution Effect.2002

    • Author(s)
      Hiromi Taji.
    • Journal Title

      Organic Letters 4

      Pages: 2699-2702

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Absolute Configuration of 2-Methoxy-2-(1-naphthyl)propionic and 2-Methoxy-2-(2-naphthyl)propionic Acids as Determined by the Phenylglycine methyl Ester (PGME) Method.2002

    • Author(s)
      Akio Ichikawa.
    • Journal Title

      Tetrahedron : Asymmetry 13

      Pages: 1167-1172

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] Novel Chiral Derivatizing Agents Powerful for Enantioresolution and Descrimination of Absolute Stereochemistry by X-Ray Crystallographic and 1H NMR Anisotropy Methods.2004

    • Author(s)
      Nobuyuki Harada
    • Publisher
      Elssevier Science Publishers, Amsterdam(印刷中)
    • Related Report
      2004 Annual Research Report
  • [Book] Chiral Analysis, Novel Chiral Derivatizing Agents Powerful for Enantioresolution and Determination of Absolute Stereochemistry by X-ray Crystallographic and 1H NMR Anisotropy Methods.

    • Author(s)
      Nobuyuki Harada
    • Publisher
      Elsevier Science Publishers, Amsterdam.(in press)
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] Chiral Analysis, Novel Chiral Derivatizing Agents Powerful for Enantioresolution and Determination of Absolute Stereochemistry by X-Ray Crystallographic and 1H NMR Anisotropy Methods.

    • Author(s)
      Nobuyuki Harada.
    • Publisher
      Elsevier Science Publishers, Amsterdam (in press)
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 第三級カルボン酸類の光学分割法2005

    • Inventor(s)
      原田宣之, 田地宏美, 内藤順平, 桑原俊介, 渡辺政隆
    • Industrial Property Rights Holder
      東京化成工業株式会社
    • Industrial Property Number
      2005-182552
    • Filing Date
      2005-05-27
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Masashi Kosaka, Takeo Sugito, Yusuke Kasai, Shunsuke Kuwahara, Masataka Watanabe, Nobuyuki Harada, Gabriel E.Job, Alex Shvet, William H.Pirkle: "Enantioresolution and Absolute Configurations of Chiral meta-Substituted Diphenylmethanols as Determined by X-ray Crystallographic and 'H NMR Anisotropy Methods"Chirality. 15(4). 324-328 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Kasai Y., Watanabe M., Harada N.: "Convenient Method for Determining the Absolute Configuration of Chiral Alcohols with Racemic 'HNMR Shift Reagent, MaNP Acid. Use of HPLC-CD Detector"Chirality. 15. 295-299 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Ito S., Yokoyama R., Okujima T., Terazono T., Kubo, T., Tajiri A., Watanabe, M., Morita, N.: "Reaction of azulenes with 1-trifluoromethanesulfonylpyridinioum trifluoromethanesulfonate (TPT) and synthesis of the parent azulene"Org.Biomol.Chem.. 1. 1947-1952 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Ito S., Kubo T., Kondo M., Kabuto C., Morita N., Asao T., Fujimori K., Watanabe, M., Harada N., Yasunami M.: "Synthesis, stability and bonding situation of tris-, bis, andmono[9-(azuleno[bis1,2-b]thienyl)]methyl cations"Org.Biomol.Chem.. 1. 2572-2580 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Tto S., Moriyama M., Nakashima M., Watanabe M., Kubo T., Yasunami M., Fujimori K., Morita N.: "Synthesis of azuleneheterocyclic compounds using 2-(2-azulenyl)-ethynyltriphenylphosphoniumbromide"Heterocycles. 61. 339-348 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] NAITO J., KOSAKA M., SUGITO T., WATANABE M., HARADA N., PIRKLE W.H.: "Enantioresolution of Fluorinated Diphenylmethanols and Determination of Their Absolute Configurations by X-Ray Crystallographic and 'H NMR Anisotropy Methods"Chirality. 16. 22-35 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Kasai, Y., Watanabe, M., Harada, N.: "Convenient Method for Determining the Absolute Configuration of Chiral Alcohols with Racemic ^1H NMR Shift Reagent, MaNP Acid, Use of HPLC-CD Detector."Chirality. 15. 324-328 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kosaka, M., Sugito, T., Kuwahara, S., Watanabe.M., Harada, N., Job, G.E., Pirkle, W.M.: "Enantioresolution and Absolute Configurations of Chiral meta-Substituted Diphenylmethanols As Determined by thr X-ray Crystallographic and ^1H NMR Anisotropy Methods"Chirality. 15. 295-299 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Fujita.T., Kuwahara, S., Watanabe M., Harada, N.: "Crystalline State Conformation of 2-(Methoxy-2(1-naphthyl)propionic Acid Ester"Enantiomer. 6. 219-223 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Ichikawa, A., Ono, H., Watanabe, M., Harada.N.: "Absolute Configuration of 2-Methoxy-2-(1-naphthyl)propionic and 2-Methoxy-2-(2-naphthvl)propionic Acid as by the Phenylalycine Methyl Ester (PGME)"Tetrahedron : Asymmetery. 13. 2699-2702 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Taji, H., Watanabe, M., Harada, N., Naoki, H., Ueda, Y.: "A Diastereomer Method for Determining %EE by ^1H NMR and/or MS Spectrometry with Complete Removal of the Kinetic Resolution Effect"Organic Lett.. 4. 1167-1172 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Ito, S., Yokoyama, Y., Asao, T., Watanabe.M., Harada.N., Morita: "Reaction of (η4-CycloheptatrieneFe(CO)_3 with Haloketenes : Structure and Reactivity of the Cycoaddcts"J. Organomet. Chem.. 48. 164-175 (2002)

    • Related Report
      2002 Annual Research Report

URL: 

Published: 2002-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi