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Transition-Metal Complex-Catalyzed Synthesis of Novel Biologically Active Amino Acids

Research Project

Project/Area Number 62550629
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

TSUDA Tetsuo  Faculty of Engineering,Kyoto University, Associate Professor, 工学部, 助教授 (10025992)

Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1988: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1987: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsAmino acid synthesis / -Allylpalladium complex having two different functional groups / CーNカップリング反応 / 二官能基化π-アリルパラジウム錯体 / C-Nカップリング反応 / 二官能性π-アリルパラジウム錯体の位置選択的反応 / π-アリルパラジウム錯体と窒素求核剤との反応
Research Abstract

Synthesis of a , -unsaturated -amino acid or , -unsaturated -amino acid derivative by the reaction of a nitrogen nucleophile with a -allylpalladium complex having hydroxyalkyl and carboxyl functional groups at both allylic carbon atoms was investigated. Palladium(O)-phosphorus ligand complexes catalyzed the reaction of methyl , -epoxysorbate with nitrogen nucleophiles such as phthalimide and benzenesulfonamide to afford regiospecifically (E)-5-hydroxy-4-amino-2-hexenoates, i.e., , -unsaturated -amino acid derivatives, in high yields. The -regiospecificity of the C-N coupling reaction was not influenced by the phosphorus ligand (P(OCH_2)_3CEt, PPh_3, PCy_3, PEt_3, dppf) and the solvent used (THF, C_6H_6-THF, DMSO, DMF). Change of the carbonyl functionality from the ester group to the amide group did not alter the -regiospecificity of the C-N coupling reaction: the palladium(O)-catalyzed reaction of N,N-diethyl- , -epoxysorbamide with phthalimide produced the corresponding -N-substituted product. Thus it was established in the present study that the palladium(O)-catalyzed reaction of , -epoxysorbic acid derivatives with nitrogen nucleophiles provides a convenient synthetic method of , -unsaturated -amino acid derivatives.

Report

(3 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • Research Products

    (3 results)

All Other

All Publications (3 results)

  • [Publications] Tetsuo Tsuda: Journal of Organic Chemistry. 54. 977-979 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tetsuo Tsuda; Yosuke Horii; Yasuyo Nakagawa; Tadashi Ishida; Takeo Saegusa: "Palladium(o)-Catalyzed Reaction of Methyl , -Epoxysorbate with Nitrogen Nucleophiles" Journal of Organic Chemistry. 54. 977-979 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tetsuo Tsuda: Journal of Organic Chemistry. 54. 977-979 (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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