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A Development of Carbon-Carbon Bond Forming Reaction without Protection of Hydroxyl Group and Carboxyl Group

Research Project

Project/Area Number 10640524
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokushima University

Principal Investigator

WADA Makoto  Tokushima University, Faculty of Integrated Arts and Sciences, Professor, 総合科学部, 教授 (10016173)

Co-Investigator(Kenkyū-buntansha) 徳島大学, 総合科学部, 教授
Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1998: ¥1,800,000 (Direct Cost: ¥1,800,000)
KeywordsAllylbismuth Reagent / Allyltin Reagent / Aqueous Media / water / Allylation Reaction / Asymmetric Allylation / c-c Bond Forming Reaction / Green Chemistry / 保護・脱保護 / カルボニル化合物 / 三塩化ビスマス / 金属ビスマス / 無保護糖 / 炭素-炭素結合生成 / ホモアリリックアルコール / アリルGrignard試薬 / ビスマス / スズ
Research Abstract

This summary presents the research results of a development of carbon-carbon bond forming reaction without protection of hydroxyl group and carboxyl group
(1) A Grignard-type additon of allyl unit to carbonyl compounds containing a carboxyl group by using bismuth trichloride-metallic zinc-allyl bromide.
(2) Allylation of aldehydes by using allylic alcohols in the presence of metallic bismuth
(3) A novel aqueous Barbier-Grignard-type allylation of aldehydes in a metallic magnesium/bismuth trichloride bimetal system.
(4) Allylation of carbonyl compounds by using allyl Grignard reagent and various metallic salts in aqueous media.
(5) Allylation of aldehydes by using allyltin compounds in aqueous media.
(6) Asymmetric allylation of carbonyl compounds by using tetraallyltin.
(7) Bismuth mediated allylation of unprotected carbohydrates.

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 和田眞、三好徳和: "ビスマスやスズ化合物を用いる有機合成ー含水溶媒中や水中での有機合成反応を中心としてー"有機合成化学協会誌. 57. 689-697 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Kimura and M.Wada: "Solvent-Mediated Chemoselective Reduction of Aldehydes by Using Tributyltin Hybride in Metanol,Aqueous Organic Solvents,or Water:An Environmentally Benign Process"Tetrahedron Letters. 40. 9059-9062 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N.Miyashi,M.Nishino,S.Murakami,T.Fukuma,and M.Wada: "A Convenient One Pot Allylation of Aldehydes with Allylic Halides Prepared in situ from Allylic Alcohols in the Presence of Metallic Bismuth"Bull.Chem.Soc.Jpn. 73. 689-692 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Wada and N. Miyoshi: "Organic Synthesis by Using Bismuth and Tin Compounds : Synthetic Organic Reactions in Aqeous Media or Water"J. Syn. Org. Chem. Jpn.. 57. 689-697 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kamiura and M. Wada: "Solvent-Mediated Chemoselective Reduction of Aldehydes by Using Tributyltin Hydride in Methanol, Aqueous Organic Solvents, or Water : An Environmentally Benign Process"Tetrahedron Letters. 40. 9059-9062 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N. Miyoshi, M. Nishio, S. Murakami, T. Fukuma, and M. Wada: "A Convenient One Pot Allylation of Aldehydes with Allylic Halides Prepared in situ from Allylic Alcohols in the Presence of Metallic Bismuth"Bull. Chem. Soc.. 73. 689-692 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 和田眞,三好徳和: "ビスマスやスズ化合物を用いる有機合成-含水溶媒中や水中での有機合成反応を中心として-"有機合成化学協会誌. 57. 689-697 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Kamiura and M.Wada: "Solvent-Mediated Chemoselective Reduction of Aldehydes by Using Tributylin Hydride in Methanol,Aqueous Organic Solvents,or Water: An Environmentally"Tetrahedron detters. 40. 9059-9062 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] N.Miyoshi,M.Nishio,S.Murakami,T.Fukuma,and M.Wada: "A Convenient One Pot Allylation of Aldehydes with Allylic Halides Prepared in situ from Allylic Alcohols in the Presence of Metallic Bismuth"Bull.Chem.Soc.Jpn. 73. 689-692 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] 和田眞: "ビスマスやスズ化合物を用いる有機合成-含水溶媒中や水中での有機合成反応を中心にして-" 有機合成化学協会誌. 57. (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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