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Transformation of Biomass Based on S_N2 Reaction of Carbon-Heteroatom Bond

Research Project

Project/Area Number 19750077
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

HATAKEYAMA Takuji  Kyoto University, 化学研究所, 助教 (90432319)

Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥3,690,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2007: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywords触媒・化学プロセス / バイオマス / 有機化学 / 芳香族アミン
Research Abstract

糖及びアミノ酸誘導体の直接的精密分子変換を目的とし,高活性マグネシウムエナミドを用いた,炭素-ヘテロ原子結合のSN2置換反応の開発に着手した.エナミドの窒素上置換基,溶媒,温度,濃度など,種々の条件を検討した結果,2級のフッ化アルキル及び2級のアルキルトシラートに対するS_N2反応が効率的に進行することが明らかとなった.一方で,2級のアルキルアミン誘導体を用いた場合,置換反応は進行しなかった.そこで,アリールグリニャール試薬を用いた鉄触媒クロスカップリング反応を検討した結果,炭素-窒素結合の切断に伴う炭素-炭素結合生成反応が進行することを見出した.また,その研究過程で,量論量のTMEDA存在下,アリールグリニャール試薬がクロロアミンに対して求核置換反応を起こすことを見出した.これらの手法は,天然に豊富に存在するアミノ酸やアルカロイド類の簡便な分子骨格変換と芳香族アミン類の簡便な合成において有用性が期待できる.

Report

(3 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • Research Products

    (11 results)

All 2009 2008 2007 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (2 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Diastereoselective Addition of Zincated Hydrazones to Alkenylboronates and Stereospecific Trapping of Boron/Zinc Bimetallic Intermediates by Carbon Electrophiles2008

    • Author(s)
      畠山琢次,中村正治,中村栄一
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 15688-15701

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Diastereoselective Addition of Zincated Hydrazones to Alkenylboronates and Stereospecific Trapping of Boron/Zinc Bimetallic Intermediates by Carbon Electrophiles2008

    • Author(s)
      Hatakeyama, T. ; Nakamura, M. ; Nakamura, E.
    • Journal Title

      J. Am. Chem. Soc 130

      Pages: 15688-15701

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective alpha-Alkylation of Ketones with Alkyl Chlorides and Fluorides via Highly Nucleophilic Magnesium Enamides2007

    • Author(s)
      畠山琢次,伊藤慎庫,山根宏明,中村正治,中村栄一
    • Journal Title

      Tetrahedron 63

      Pages: 8440-8448

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed 2-Alkenylation of 1,3-Dicarbonyl Compounds with Unactivated Alkynes2007

    • Author(s)
      遠藤恒平,畠山琢次,中村正治,中村栄一
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 5264-5271

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective alpha-Alkylation of Ketones with Alkyl Chlorides and Fluorides via Highly Nucleophilic Magnesium Enamides2007

    • Author(s)
      Takuji Hatakeyama, Shingo Itoh, Hiroaki Yamane, Masaharu Nakamura, Eiichi Nakamura
    • Journal Title

      Tetrahedron 63

      Pages: 8440-8448

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] N-クロロアミンの求核的アリール化による芳香族アミン類の合成法の開発2008

    • Author(s)
      吉本祐也・Ghorai Sujit・畠山琢次・中村正治
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2008-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] N-クロロアミンの求核的アリール化による芳香族アミン類の合成法の開発

    • Author(s)
      吉本祐也, Ghorai Sujit, 畠山琢次,中村正治
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://es.kuicr.kyoto-u.ac.jp/

    • Related Report
      2008 Final Research Report
  • [Patent(Industrial Property Rights)] 芳香族アミン化合物の製造方法2009

    • Inventor(s)
      畠山琢次・中村正治・吉本祐也
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2009-058274
    • Filing Date
      2009-03-11
    • Related Report
      2008 Final Research Report
  • [Patent(Industrial Property Rights)] 多環芳香族化合物2009

    • Inventor(s)
      畠山琢次・中村正治・橋本士雄磨
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2009-057421
    • Filing Date
      2009-03-11
    • Related Report
      2008 Final Research Report
  • [Patent(Industrial Property Rights)] 芳香族アミン化合物の製造方法2009

    • Inventor(s)
      中村正治・畠山琢次・吉本祐也
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2009-058274
    • Filing Date
      2009-03-11
    • Related Report
      2008 Annual Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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