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The developnent of New Synthetic Methods Based on Sulfoxide-Metal Exchange

Research Project

Project/Area Number 11640545
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionScience Uhiversity of Tokyo

Principal Investigator

TSUYOSHI Satoh  Facility of Science, Science Uhiversity of Tokyo professor, 理学部, 教授 (20089329)

Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1999: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordscarbanion / carbenoid / magnesium carbenoid / sulfoxide / cyclopentenone / enaminonitrile / allene / carboxylic acid / リガンド交換反応 / アルキリデンカルベノイド / マグネシウムシクロプロピリデン / アジリジニルマグネシウム / 不斉合成 / ホモロゲーション / アジリジニルリチウム
Research Abstract

1.The reaction of the sulfinylaziridines with a Griguard reagent gave the aziridinylmagnesiums. Cross coupling of this aziridinymagnesiumes with alkylhalides catalyzed by Cu(I) iodide gave the alkylated aziriHines, from which the asymmetric synthesis of act-disubstituted p-amiho acids was realized.
2.Addition of cyanomethyllithium to 1-chloroyinyl p-tolyl sulfoxides gave the cyclopentadiehyl enaininonitriles in high yields. A novel synthesis of optically active 4, 4-disubstituted cyclopentenone derivatives was established from the enaminonitriles.
3.A new synthesis of highly functionalized carboxylic acid derivatives was realized from 1-chlorovinyl p-tolyl sulfoxides and lithium enolate of acetic acid esters.
4.A new method for generation of magnesium cyclopropylidenes and a synthesis of alkylidenecyclopropanes was realized.
5.A new method for the synthesis ofallenes through the magnesium alkylidene carbenoids was established.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] T.Satoh: "Aryl 1-chloroalkyl sulfoxides as acyl anion equivalent : a new synthesis of vinyl"Tetrahedron. 57. 493-500 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "Cross-coupling of nonstabilized aziridinyl mangnesiums with alkylhalides catalyzed"Tetrahedron. 57. 3891-3898 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "Magnesium cyclopropylidenes generated from 1-chlorocyclo proplyphenyl sulfoxides with"Tetrahedron. 57. 5369-5375 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "A new synthesis of β,γ-alkenyl carboxylic acids from α,β0alkenyl carboxylic acid chlorides"Tetrahedron. 57. 9689-9696 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "Asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active"Tetrahedron Letters. 42. 9241-9244 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "A nobel synthesis of allenes by alkenylation of magnesium alkylidene carbenoids"Tetrahedron Letters. 43(in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, D. Taguchi, C. Suzuki, S. Fujisawa: "Aryl 1 -chloroalkyl sulfoxides as acyl anion equivalents ; asmew synthesis of vinyl silfides, ketones, and diketones from aryl 1 -chloroalkyl sulfoxides and"Tetrahedron. Vol.57. 493-500 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, R. Matsue, T. Fujii, S. Morikawa: "Cross-coupling of nonstabilized aziridinylmagnesiums with alkylhalides catalyzed by Cu( : I) iodide : a new synthesis of amines bearing a quaternary chiral center and an asynroetric synthesis of both"Tetrahedron. Vol.57. 3891-3898 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, T. Kurihara, K, Fujita: "T. Satoh, T. Kurihara, K, Fujita"Tetrahedron. Vol.57. 5369-5375 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, A. Nakamura, A. Iriuchijima, Y. Hayashi, K. Kubota: "A new synthesis of β, γ-aikenyl carboxylic acids from α, β.-alkenyl carlDoxylic acid chlorides and α, β-alkenyl aldehydes with one-carbon elongation"Tetrahedron. Vol.57. 9689-9696 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, M. Yoshida, H. Ota: "Asymmetric synthesis of 4, 4-disubstituted 2-cycldpentenones from optically active 1 -chlorovinyl p-tolyl sulfoxides, and cyanomethyllithium with formation of ; a quaternary chiral center"Tetrahedron Letters. Vol.42. 9241-9244 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Satoh, T. Sakamoto, M. Watanabe: "A Hovel synthesis of allenes by alkenyl-ation of magnesium alkylidene carbenoids with lithium α-sulfonyl carbanions"Tetrahedron Lettes. Vol.43(in press). (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Satoh: "Aryl 1-chloroalkyl sulfoxides as acyl anion equivalent:a new synthesis of vinyl……"Tetrahedron. 57. 493-500 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh: "Cross-coupling of nonsabilized aziridinyl-magnesiums with alkylhalides catalyzed……"Tetrahedron. 57. 3891-3898 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh: "Magnesium cyclopropylidenes generated from 1-chlorocyclopropyl phenyl sulfoxides with……"Tetrahedron. 57. 5369-5375 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh: "A new synthesis of β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic carboxylic acid chlorides……"Tetrahedron. 57. 9689-9696 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh: "Asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active……"Tetrahedron Letters. 42. 9241-9244 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh: "A novel synthesis of allenes by alkenylation of magnesium alkylidene carbenoids……"Tetrahedron Letters. 43(in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Satoh er al.: "A new method for the synthesis of α-thio aldehydes and alcohols from aldehydes…"Tetrahedron Letters. 41. 2121-2124 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "Generation of aziridinyllithiums from sulfinylaziridines with tert-butyllithiums…"Tetrahedron. 56. 4415-4425 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "Reaction of l-chlorovinyl p-tolyl sulfoxides with carbanion of acetonitrile : A novel…"Tetrahedron. 56. 5113-5122 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "Alkylation of nonstabilized aziridinyl magnesiums catalyzed by Cu(I) iodide : A new synthesis…"Tetrahedron Letters. 41. 6495-6499 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "A sulfoxide version of the Julia-Lythgoe olefination : A new method for the…"Tetrahedron. 56. 6223-6234 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "Aryl l-chloroalkyl sulfoxides as acyl anion equivalents : A new synthesis of vinyl…"Tetrahedron. 57. 493-500 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Satoh et al.: "A new method for synthesis of allenes,including an optically active torm,from aldehydes・・・・"Tetrahedron Letters. 40. 8815-8818 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Satoh: "スルホキシド-金属交換反応を利用する有機合成"ファルマシア. 35・12. 1225-1229 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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