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New Development of Synthetic Reactions using Organoselenoboranes and Application to Synthesis of Pharmacologically Active Compounds

Research Project

Project/Area Number 02670959
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionGifu Pharmaceutical University

Principal Investigator

KATAOKA Tadashi  Gifu Pharm. Univ. Professor, 薬学部, 教授 (00082975)

Co-Investigator(Kenkyū-buntansha) YOSHIMATSU Mitsuhiro  Gifu Pharm. Univ. Assistant, 薬学部, 助手 (80240349)
IWAMURA Tatsunori  Gifu Pharm. Univ. Assistant, 薬学部, 助手 (70184900)
SHIMIZU Hiroshi  Gifu Pharm. Univ. Associate Professor, 薬学部, 助教授 (00082983)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1991: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1990: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsOrganoselenium Compound / Selenoborane / Radical Addition / Radical Cyclization / C-O Bond Cleavage / Cyclic Ether / alpha-Seleno Carbocation / Diselenoacetal / トリス(フェニルセレ)ノボラン / トリス(メチルセレ)ノボラン / メチレンシクロペンタン / ジセレノアセタ-ル / セレニルラジカル / エ-テル結合開裂 / テトラヒドロフラン / ジヒドロピラン
Research Abstract

(1)Tris(phenylseleno)borane or tris(methylseleno)borane added to the terminal triple bonds and vinyl selenides were formed. This addition reaction was initiated by oxygen and proceeded by the radical process. The reaction mechanism was investigated by ^1H- and ^<11>B-NMR spectroscopy.
(2)This reaction was applied to the cyclization reaction of enynes containing a nitrogen, an oxygign or a sulfur atom. The intramolecular ring closure of the vinyl radical intermediate to the double bond proceeded preferentially via 5-exo mode of cyclization and the nitrogen, oxygen or sulfur-heterocycles were diastereoselectively given. in good yields.
(3)Tris(phenylseleno)borane underwent the C-O bond cleavage of the tetrahydrofuran and tetrahydropyran derivatives in the presence of zinc chloride or tin(IV)chloride to give omega-phenylseleno alcohols in excellent yields.
(4)Treatment of diselenoacetals with a Lewis acid generated the alpha-seleno carbocations. The olefinic alpha-seleno carbocations underwent the endo-selective ring-closure.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Tadashi Kataoka: "Vinyl Radical Generation with Selenoborane and Its Application to Cyclization Reaction of Eneynes" Tetrahedron Letters. 31. 5927-5930 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka: "The C-O Bond Cleavage of Cyclic Ethers with Tris(phenylseleno)-borane-Lewis Acid" Heterocycles. 31. 889-893 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka: "Endo Selective Cyclizations of Selenonium Ion Intermediate:Efficient Formatin of 1-Halo-3-selenocyclohexanes" Tetrahedron Letters. 32. 105-108 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka, Mitsuhiro Yoshimatsu, Hiroshi Shimizu, and Mikio Hori: "Vinyl Radical Generation with Selenoborane and Its Application to Cyclization Reaction of Eneynes" Tetrahadron Lett.31. 5927-5930 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka, Mitsuhiro Yoshimatsu, Hiroshi Shimizu, Yoshitaka Kawase, and Mikio Hori: "The C-O Bond Cleavage of Cyclic Ehters with Tris (phenylseleno) borane-Levis Acid" Heterocycles,. 31. 889-893 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka, Mitsuhiro Yoshimatsu, Hiroshi Shimizu, and Mikio Hori: "Endo Selective Cyclizations of Selenonium Ion Intermediate : Efficient Formation of 1-Halo-3-seleno-cyclohexanes" Tetrahedron Lett.32. 105-108 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Tadashi Kataoka: "Endo Selective Cyclizations of Selenonium Ion Intermediate:Efficient Formation of 1ーHaloー3ーselenocyclohexanes" Tetrahedron Letters. 32. 105-108 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tadashi Kataoka: "Vinyl Radical Generation with Selenoborane and Its Application to Cyclization Reaction of Enynes" Tetrahedron Letters. 41. 5927-5930 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Tadashi Kataoka: "The Cー0 Bond Cleavage of Cyclic Ethers with Tris(phenylseleno)boraneーLewis Acid" Heterocycles. 31. 889-893 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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