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Asymmetric Synthesis and Use of

Research Project

Project/Area Number 62550634
Research Category

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

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

Principal Investigator

UTAKA Masanori  Faculty of Engineering, Okayama University, 工学部, 教授 (30033153)

Co-Investigator(Kenkyū-buntansha) SAKAI Takashi  Faculty of Engineering, Okayama University, 工学部, 助手 (00170556)
TSUBOI Sadao  Faculty of Engineering, Okayama University, 工学部, 助教授 (00032954)
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)
KeywordsOptically active -chloro acids / Optically active 2,4,4-trichlorobutanoic acid / Asymmetric synthesis of both enantiomers / 両鏡像体合成 / パン酵母還元 / ロイシノピンアナログ / クラウンゴール / 不斉還元 / パン酵母 / 光学活性α-ハロエステル / α-アミノ酸 / α-クロローα, β-不飽和エステル
Research Abstract

Asymmetric reduction of (E)- and (Z)-methyl 2-chloro-2-alkenoates by use of fermenting bakers' yeast gave (R)- and (S)-2-chloroalkanoiceacids in 25 92% ee and 98% ee, respectively. The chemical yields were 10 40% for 2-chloropentenoate, 2-chloroheptenoate, but 65 70% for 2,4,4-trichloro- and 2,4,4,4-tetrachlorobutenoates. The substrates were found to be reduced after hydrolysis to the acids. The reactivity and stereoselectivity of the reduction were discussed. The reduction products, (R)- and (S)-2,4,4-trichlorobutanoic acids, were transformed to (S)- and (R)-2-amino-4,4-dichlorobutanoic acids, respectively.
In order to prepare a dichloro-substituted leucinopine analog, reaction of 2-amino-4,4-dichlorobutanoic acid with -ketoglutaric acid was investigated.

Report

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

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Masanori Utaka;Satoshi Konishi;Toshiyasu Okubo;Sadao Tsuboi;Akitra Takeda: Tetrahedron Letters. 28. 1447-1450 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masanori Utaka;Satoshi Konishi;Ami Mizuoka;Toshiyasu Okubo;Takashi Sakai;Sadao Tsuboi;Akira Takeda: Journal of Organic Chemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masanori Utaka;Hiroshi Matsubara;Hisashi Watabu;Takashi Sakaii Sadao Tsuboi: Journal of Organic Chemistry.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masanori,Utaka; Satoshi,Konishi; Toshiyasu,Okubo; Sadao,Tsuboi; Akira,Takeda: "A facile Synthesis of Optically Pure L-Armentomycin and Its D-Isomer. Highly Enantioselective Reduction of the C-C Double Bond of Methyl (E)- and (Z)-2,4,4-Trichloro-2-butenoate by Using Bakers' Yeast" Tetrahedron Letters. 28. 1447-1450 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masanori,Utaka; Satoshi,Konishi; Ami,Mizuoka; Toshiyasu,Okubo; Takashi,Sakai; Sadao,Tsuboi; Akira,Takeda: "Asymmetric Reduction of the Prochiral Carbon-Carbon Double Bond of Methyl 2-Chloro-2-alkenoates by Use of Fermenting Bakers' Yeast" Journal of Organic chemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masanori,Utaka; Hiroshi,Matsubara; Hisashi,Watabu; Takashi,Sakai; Sadao,Tsuboi: "Separation and Characterization of Four Diastereomers of Leucinopine" Journal of Organic Chemistry.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 宇高正徳、小西聡、水岡亜美、大久保利恭、酒井貴志、坪井貞夫、武田晃: Journal of Organic Chemistry. 54. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 宇高正徳、松原広、渡部久、酒井貴志、坪井貞夫: Journal of Organic Chemistry. 54. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masanori Utaka;Satoshi Konishi;Toshiyasu Okubo;Sadao Tsuboi;Akira Takeda: Tetrahedron Letters. 28. 1447-1450 (1987)

    • Related Report
      1987 Annual Research Report

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

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