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1999 Fiscal Year Final Research Report Summary

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
KeywordsAllylbismuth Reagent / Allyltin Reagent / Aqueous Media / water / Allylation Reaction / Asymmetric Allylation / c-c Bond Forming Reaction / Green Chemistry
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.

  • Research Products

    (6 results)

All Other

All Publications (6 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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2001-10-23  

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