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1996 Fiscal Year Final Research Report Summary

Study on Electron Transfer Reaction on Electrode aimed at Nitrogen Atomcontaining Pharmaceuticals

Research Project

Project/Area Number 07455364
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

MATSUMURA Yoshihiro  Nagasaki University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (60026309)

Co-Investigator(Kenkyū-buntansha) WATANABE Mitsuaki  Nagasaki University, Center for Instrumental Analysis, Associate Prof., 計測分析センター, 助教授 (10039654)
KINOSHITA Toshio  Nagasaki University, Pharmaceutical Sciences, Associate Prof., 薬学部, 助教授 (60039641)
Project Period (FY) 1995 – 1996
KeywordsElectrochemical Oxidation / Carbamates / Substitutent Effect / Asymmetric Synthesis / Proline / Piperidine Derivatives
Research Abstract

We have studied in detail on the electron transfer reactions from carbamates to electrode in order to efficiently apply the electochemical reactions to fine organic synthesis which involves nitrogenatom containing pharmaceuticals. The following results were obtained.
1) Electorhchemical oxidation of proline ester and asymmetric synthesis : Electrochemical oxidation of N-methoxycarbonylated proline ester in methanol was carried out to see the regioselectivity, that is, selectivity of the oxidation at alpha-and alpha'-positions, and optically active alpha-alkylprolines were prepared by use of the oxidation products.
2) beta-Substituent effect on electron transfer reaction : Electrochemical oxidation of carbamates possessing a halogen atom or a methoxycarbonyl group at the beta-position was investigated in order to clarify the substituent effect on the electron transfer reaction, and it was found that such electron-withdrawing substituents did not give much effect on the electron transfer type oxidation. As the results, a-substituted aziridines could be synthesized utilizing the oxidation products.
3) Introduction of substituent on gamma-position of piperidine ring : Asymmetric introduction of an alkyl group into the gamma-position of piperidine ring was achieved by use of the electrochemical oxidation products of N-methoxycarbonylpiperidine.
4) Application to fine organic synthesis : The following three projects, i) diastereoselective synthesis of 3-amino-2-hydroxyalkanecarboxylic acids using electrochemical oxidation products, ii) synthesis of enamines possessing a variety of functional groups from primary amines, and iii) preparation of optically active beta-hydroxyamines from primary amines, were achieved.

  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] N,Kise: "Diastereoselective Synthesis of 3-Amino-2-Hydroxyalkanoic Acid Derivatives" Tetrahedron Letters. 36. 909-912 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y,Matsumura: "Regio-and Stereo-selective Introduction of a Bis(methoxycarbonyl)methyl Group into the γ-Position of the Piperidine Skeleton" Tetrahedron Letters. 37. 5715-5718 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y,Matsumura: "New Synthetic Method of Optically Active α-Methylproline and α-Methyl-pipecolinic Acid using Electrochemical Oxidation as a Key Reaction" Tetrahedron Letters. 37. 8395-8398 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y,Matsumura: "A Convenient Method for Synthesis of Optically Active β-Hydroxyamines from Primary Amines through Enecarbamates as Key Intermediates" Tetrahedron. 53(印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Kise, N.Inakoshi, and Y.Matsumura: "Diastereo selective Synthesis of 3-Amino-2-Hydroxyalkanoic Acid Derivatives" Tetrahedron Lett.36 (6). 909-912 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Matsumura, Y.Yoshimoto, C.Horikawa, T.Maki, and M.Watanabe: "Regio-and Stereo-selective Introduction of a Bis (methoxycarbonyl) methyl Group into the gamma-Position of the Piperidine Skeleton" Tetrahedron Lett.37. 5715-5718 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Matsumura, T.Kinoshita, Y.Yanagihara, N.Kanemoto, and M.Watanabe: "New Synthetic Method of Optically Active alpha-Methylproline and alpha-Methylpipecolinic Acid using Electrochemical Oxidation as a Key Reaction" Tetrahedron Lett.37. 8395-8398 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Matsumura, T.Ohishi, C.Sonoda, M.Watanabe: "A Convenient Method for Synthesis of Optically Active beta-Hydroxyamines from Primary Amines through Enecarbamates as Key Intermediates" Tetrahedron. in press. (1997)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-03-09  

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