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DEVELOPMENT OF NEW REGIO AND STEREOSELECTIVE REACTIONS FOR ORGANIC SYNTHESIS

Research Project

Project/Area Number 61470025
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKyoto University

Principal Investigator

KAJI Aritsune  Professor (Faculty of Science), 理学部, 教授 (10025223)

Co-Investigator(Kenkyū-buntansha) TANAKA Kazuhiko  Assistant (Faculty of Science), 理学部, 助手 (00025446)
TANIKAGA Rikuhei  Assistant Professor (Faculty of Science), 理学部, 助教授 (60025377)
小野 昇  京都大学, 理学部, 助教授 (40093215)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥6,500,000)
Fiscal Year 1987: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1986: ¥6,000,000 (Direct Cost: ¥6,000,000)
KeywordsALKYLATION OF FURAN / DENITRO-ALKYLATION / ORIENTATION CONTROL OF DIELS-ALDER REACTION / SYNTHON OF ALKYNE / CYCLOPROPANECARBOXYLIC ACID / HOMOBUTENOLIDE / YEAST REDUCTION OF KETON / 不斉アルコール合成 / ニトロ基の脱離 / エピスルホニウム / 分子内フリーデルクラフト反応 / シクロプロパン合成 / ブテノリド / 不斉アルコールの合成 / 酵母還元 / ニトロフラン / イースト還元 / ケトンの不斉還元 / ジアニオン / メタクリル酸アニリド / アセチレンのシントン / ニトロアルケン
Research Abstract

The research has been successfully performed as follows:
1. Substitution of Nitro Group on Nitrofurancarboxylic Esters: Ethyl 2-nitrofuran-5-carboxylate were easily converted to ethyl 3-alkylfuran-5-carboxylate by the reaction with an anion of nitroalkane followed by the treatment with tributyltin hydride. THus, a new denitro-alkylation reaction on furan has been presented.
2. New Orientation Control on the Deils-Alder Reaction: 1-Nitro-2-phenylsulfonyl-1-alkenes were found to be strong dienophile. It reacted with 2-methyl-2-butene to give a cyclohexene. The product was treated with tributyltin hydride to give 1-methyl-4-alkylcyclohexa-1,4-diene only.
3. New Convenient Synthesis of Cyclopropanecarboxylic Acid: When 2-phenylthionethyl-3-phenylthiopropioanilide was converted to its dianion, 2-phenylthiocyclopropanecarbanilide was obtained spontaneously. The product could be derived to highly functional derivatives by the reaction of its dianion and and electrophiles such as aldehydes.
4. New Synthesis of Optically Active Alkohols with 100% Enantio Excess (e.e.): 1-Chlosyl-3-chloroacetone was easily reduced by commercial Baker's Yeast to give (R)-1-chlosyl-o-chloropropan-2-ol with 100% e.e.. The yield was 85%. This propanol could be alkylated at 3-position via its epoxide with nucleophile, and also successfully be alkylated at 1-position via its dianion. In both of the alkylation, the configuration of alcohol was kept at 100% e.e..

Report

(3 results)
  • 1988 Final Research Report Summary
  • 1987 Annual Research Report
  • 1986 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] N.Ono,;X.J.Tuo,;A.Kaji: 1)Synthesis. 821 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N.Ono,;A.Kamimura,;A.Kaji.: 2)Tetrahedron Lett.27. 1595-1598 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N.Ono,;A.Kamimura,;H.Sasatani,;A.Kaji.: J.Org.Chem.52. 4133-4135 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K.Tanaka,;K.Minami,;A.Kaji: 3)Chem.Lett.809-810 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] R.Tanikaga,;K.Hosoya,;A.Kaji.: 4)Synthesis. 389 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] R.Tanikaga,;K.Hosoya,;K.Hamamura,;A.Kaji.: 5)Tetrahedron Lett.28. 3705-3706 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N. Ono,;X. J. Tuo,;A. Kaji.: "Alkylation of Furans Via cine-Substitution of -Nitrofurans with Anions of Nitroalkanes and Subsequent Denitration" Synthesis. 821 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N. Ono,;A. Kamimura,;A. Kaji.: " -Sulfonylnitroolefins as Very Reactive Alkyne Equivalents in Diels-Alder Reactions" Tetrahedron Lett.27. 1595-1598 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] K. Tanaka,;K. Minami,;A. Kaji.: "A Short, Efficient, Stereoselective Synthesis of Functionalized Cyclopropanes through the Cyclization of N-Phenyl-3-phenylthio-2-(phenylthiomethyl)propanamide" Chem. Lett.809-810 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] R. Tanikaga,;K. Hosoya,;A.Kaji.: "Synthesis of Enantiomerically Pure (4S)-2-Alken-4-olides via (2S)-1-Phenyl-sulfonyl-2-alkanols" Synthesis. 389 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] R. Tanikaga,;K. Hosoya,;K. Hamamura,;A. Kaji.: "Stereochemistry in Alkylation of Dianions of -Hydroxysulfoxides and - Hydroxysulfones" Tetrahedron Lett.28. 3705-3706 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N.Ono;A.Kamimura;H.Sasatani;A.Kaji: J.Org.Chem.52. 4133-4135 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] K.Tanaka;K.Minami;A.Kaji: Chem.Lett.809-810 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] R.Tanikaga;K.Hosoya;A.Kaji: Synthesis. 389 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] R.Tanikaga;K.Hosoya;K.Hamamura;A.Kaji: Tetrahedron Lett.28. 3705-3706 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Noboru Ono: Synthesis. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Rikuhei,Tanikaga: J.Chem.Soc.,Chem.Commun.836-837 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 田中和彦: 日本化学会誌. N .7, (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Noboru,Ono: J.Org.Chem.51. 2140-2142 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Noboru,Ono: Tetrahedron Letters. 27. 1595-1598 (1986)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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