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2002 Fiscal Year Final Research Report Summary

Superacid-catalyzed reactions and the application of supercritical fluid

Research Project

Project/Area Number 13554023
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

OHWADA Tomohiko  Graduate School of Pharmaceutical Sciences, The University of Tokyo, Professor, 大学院・薬学系研究科, 教授 (20177025)

Project Period (FY) 2001 – 2002
Keywordssuperacids / aromatic compounds / Pictet-Spengler reaction / CO2 supercritical fluid / stereoselction / Superelectrophile / intramolecular cyclization / nitroalkanes
Research Abstract

New superacid-catalyed reactions and their features such as regioselectivity and stereoseterctivity were studied. Destabilized carbenium ions substituted with genuine electron-withdrawing groups such as carbenium, oxonium, ammonium groups were proposed to be involved. These cations constitute reactive superelectrophiles in a novel type of Friedel-Crafts reactions. We attempted to use CO_2 supercritical fluid conditions with a combination of superacid catalyst. We understood the development of new reaction system compatible with the superacid. We studied (1) Regioselective Superacid-Catalyzed Electrocyclization of Diphenylmethyl Cations. Fluorenes, Phenanthrol and Benzofuran Cyclizations (2) Stereoselectivity of Superacid-Catalyzed Pictet-Spengler Cyclization Reactions (3) 4H-l,2-Benzoxazines with Electron-withdrawing Substituents on the Benzene Ring. Synthesis and Application as Potent Intermediates for Oxygen-Functionalized Aromatic Compounds

  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] Yoshida, N., Ohwada, T.: "Regioselective Superacid-Catalyzed Electrocyclization of Diphenylmethyl Cations. Fluorenes, Phenanthrol and Benzofuran Cyclizations"Synthesis. 1487-1494 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura, S., Uchiyama, M., Ohwada, T.: "4H-1,2-Benzoxazines with Electron-withdrawing Substituents on the Benzene Ring. Synthesis and Application as Potent Intermediates for Oxygen-Functionalized Aromatic Compounds"J. Am. Chem. Soc.. (in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nakamura, S., Tanaka, M., Taniguchi, T., Uchiyama, M., Ohwada, T.: "Stereoselectivity of Superacid-Catalyzed Pictet-Spengler Cyclization Reactions"Organic Letters. (in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshida N., Ohwada.T.: "Regioselective Superacid-Catalyzed Electrocyclization of Diphenylmelhyl Cations. Fluorenes, Phenanthrol and Benzofuran Cyclizations"Synthesis. 1487-1494 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nakamura, S., Uchiyama, M., Ohwada, T.: "4H-1,2-Benzoxazines with Electron-withdrawing Substituents on the Benzene Ring. Synthesis and Application as Potent Intermediates for Oxygen-Functionalized Aromatic Compounds"J. Am. Chem. Soc.. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nakamura, S., Tanaka, M., Taniguchi, T., Uchiyama, M., Ohwada, T.: "Stereoselectivity of Superacdd-Catalyzed Pictet-Spengler Cyclization Reactions"Organic Letters.. in press. (2003)

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

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Published: 2004-04-14  

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