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2001 Fiscal Year Final Research Report Summary

DEVELOPMENT OF HIGHLY CHEMOSELECTIVE DEPROTONATION USING ZINCATES

Research Project

Project/Area Number 12672047
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

KONDO Yoshinori  TOHOKU UNIVERSITY, GRADUATE SCHOOL OF PHARMACEUTICAL SCIENCES, PROFESSOR, 大学院・薬学研究科, 教授 (90162122)

Project Period (FY) 2000 – 2001
KeywordsORGANOZINCATES / DEPROTONATION / HYDROGEN-ZINC EXCHANGE REACTION / AROMATIC COMPOUNDS / NITROGEN HETEROAROMATICS / a-METALATION / REGIO SELECTIVITY / CARBON-CARBON BOND FORMATION
Research Abstract

As a new chemoselective deprotonative agent, TMP-zincate was designed. The agent was found to be easily prepared using LTMP and di-tert-butylzinc. The agent is stable ate complex and can be used for the selective metalation of functionalized aromatic compounds with electrophilic groups. Various electrophiles were reacted with the arylzincates prepared by this deprotonation, and the scope and limitation of the methodology was disclosed. The reaction was successfully applied for the deprotonation of heteroaromatic compounds such as pyridines, isoquinolines, quinolines, and other nitrogen heteroaromatics. On the metalation of substituted pyridines, unique regioselectivity was observed and a-metalation predominates when 2-halopyridines were employed for substrates. Further investigations on the origin of this regioselectivity are underway. Application of the deprotonation for solid phase synthesis was also investigated, and the possibility was examined although further optimization of reaction conditions are necessary. Relating the deprotonation, mesityllithium was found to be an another option for selective deprotonation on polymer support, and the investigation for the scope and limitation are underway.

  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] Imahori, T., Uchiyama, M., Kondo, Y., Sakamoto, T.: "Regiocontrolled cleprotonative-zincation of bromopyvidines using aminozincates"Chem. Commun. 2450-2451 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kondo, Y., Asai, M., Miura, M., Uhiyama, M., Sakamoto, T.: "Mesityllithiun as Reagent for Chomosolective Halogen-lithium Exchange Reaction"Org. Letters. 3. 13-15 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shilai, M., Uchiyama, M., Kondo, Y., Sakamoto, T.: "Preparation and Reaction of Pyridingl Tellurides"J. Heterocyclic Clom. 38. 481-484 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shilai, M., Kondo, Y., Sakamotoi, T.: "Selective metalation of thiophene and thiagole vings with magnesium amide base"J. Chem. Soc., Perkin Trans. 1. 422-444 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Imahori, T., Uchiyama, M., Sakamoto, T., Kondo, Y.: "Regiocontrolled deprotonative-zincation of bromopyridines using aminozincates"Chem Commun. 2450-2451 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kondo, Y., Asai, M., Miura, M., Uchiyama, M., Sakamoto, T.: "Mesityllithium as a Reagent for Chemoselective Halogen-lithium Exchange Reaction"Org. Lett.. 3. 13-15 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shilai, M., Uchiyama, M., Kondo, Y., Sakamoto, T.: "Preparation and Reaction of Pyridinyl Tellurides"J. Heterocyclic Chem.. 38. 481-484 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shilai, M., Kondo, Y., Sakamoto, T.: "Selective metalation of thiophene and thiazole rings with magnesium amide base"J. Chem. Soc., Perkin Trans.. 1. 422-444 (2001)

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

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Published: 2003-09-17  

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