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Catalytic Asymmetric Synthesis of Cage-type Organic Compounds by New Stereo-controlled Approach

Research Project

Project/Area Number 23655091
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionWaseda University

Principal Investigator

SHIBATA Takanori  早稲田大学, 理工学術院, 教授 (80265735)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords面不斉 / 大環状化合物 / カゴ型化合物 / 不斉認識 / 不斉触媒
Research Abstract

I reported an enantioselective ortho-lithiation of achiral paracyclophanes with oxygen atoms as directed moieties at both ends of ansa-chain using a chiral lithium reagent. The reaction of an unflippable 1,n-dioxa[n]paracyclophane (n?□11) with sec- utyllithium and (-)-sparteine gave the chiral mono-lithiated product. Additional amount of sec-butyllithium gave C_2-symmetric dilithiated product. The quenching of these lithium salts by appropriate electrophiles gave various planar-chiral aracyclophanes with excellent ee. The planar-chiral mono- and diphosphines, which were prepared by the above protocols, were used as chiral ligands in transition metal-catalyzed reactions.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (22 results)

All 2013 2012 2011 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (17 results) (of which Invited: 1 results) Remarks (3 results)

  • [Journal Article] Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophane derivatives for the generation of planar chirality2012

    • Author(s)
      K. Kanda, H. Hamanaka, K. Endo, T. Shibata
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 5 Pages: 1407-1416

    • DOI

      10.1016/j.tet.2011.12.031

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] tioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition2012

    • Author(s)
      Shibata, T.; Miyoshi, M.; Uchiyama, T.; Endo, K.; Miura, N.; Monde, K.Enan
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 12 Pages: 2679-2686

    • DOI

      10.1016/j.tet.2012.01.046

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] (一般口頭発表) 不斉オルトリチオ化を利用した[n]パラシクロファン骨格を有する新規面不斉リン配位子の合成とパラジウム触媒を用いた不斉カップリングへの応用2013

    • Author(s)
      浜中理紗・神田和正・柴田高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Final Research Report
  • [Presentation] (一般口頭発表) 不斉薗頭カップリング反応による面不斉を有するパラシクロファンの高エナンチオ選択的合成2013

    • Author(s)
      大嶋祥也・浜中理紗・神田和正・柴田高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Final Research Report
  • [Presentation] (招待講演) New Approach to the Enantioselective Synthesis of Paracyclophanes2012

    • Author(s)
      T. Shibata, K. Kanda, R. Hamanaka, K. Endo
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC)
    • Place of Presentation
      Siem Reap, Combodia
    • Related Report
      2012 Final Research Report
  • [Presentation] (ポスター発表) Synthesis and Application of New Phosphine Ligands Containing Planer-chiral Paracyclophane Skeletons2012

    • Author(s)
      浜中理紗、神田和正, 遠藤恆平, 柴田高範
    • Organizer
      Symposium on Molecular Chirality ASIA 2012
    • Place of Presentation
      福岡
    • Related Report
      2012 Final Research Report
  • [Presentation] (一般口頭発表) 面不斉パラシクロファンの高エナンチオ選択的合成法の開発2012

    • Author(s)
      神田和正・浜中理紗・小池珠美・遠藤恆平・柴田高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2012 Final Research Report
  • [Presentation] 面不斉パラシクロファンの高エナンチオ選択的合成法の開発2012

    • Author(s)
      神田 和正・濵中 理紗・小池 珠美・遠藤 恆平・柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [Presentation] 不斉オルトリチオ化を利用した[n]パラシクロファン骨格を有する新規不斉リン配位子の合成と応用2012

    • Author(s)
      濵中 理紗・神田 和正・遠藤 恆平・柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学矢上キャンパス
    • Related Report
      2011 Research-status Report
  • [Presentation] (ポスター発表) Development of Highly Enantioselective Synthesis of Planar-Chiral Paracyclophanes2011

    • Author(s)
      K. Kanda, R. Hamanaka, T. Koike, K. Endo, T. Shibata
    • Organizer
      C&FC 2011
    • Place of Presentation
      奈良
    • Related Report
      2012 Final Research Report
  • [Presentation] (ポスター発表) Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophanes2011

    • Author(s)
      K. Kanda, K. Endo, T. Shibata
    • Organizer
      The 6th Global COE International Symposium on "Practical Chemical Wisdom
    • Place of Presentation
      東京
    • Related Report
      2012 Final Research Report
  • [Presentation] (一般口頭発表) エナンチオ選択的オルトリチオ化による面不斉パラシクロファン化合物群の合成法の開発2011

    • Author(s)
      神田和正,遠藤恆平, 柴田高範
    • Organizer
      モレキュラーキラリティー2011
    • Place of Presentation
      東京
    • Related Report
      2012 Final Research Report
  • [Presentation] エナンチオ選択的オルトリチオ化による面不斉パラシクロファン化合物群の合成法の開発2011

    • Author(s)
      神田 和正, 遠藤 恆平, 柴田 高範
    • Organizer
      モレキュラーキラリティー2011
    • Place of Presentation
      東京工業大学 大岡山キャンパス
    • Related Report
      2011 Research-status Report
  • [Presentation] 面不斉を有するパラシクロファンの高エナンチオ選択的合成法の確立2011

    • Author(s)
      神田和正、濵中理紗、小池珠美、遠藤恆平、柴田高範
    • Organizer
      第100回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2011 Research-status Report
  • [Presentation] Development of Highly Enantioselective Synthesis of Planar-chiral Paracyclophanes2011

    • Author(s)
      K. Kanda, R. Hamanaka, T.i Koike, K. Endo, T. Shibata
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2011
    • Place of Presentation
      奈良新公会堂
    • Related Report
      2011 Research-status Report
  • [Presentation] New Approach to the Enantioselective Synthesis of Paracyclophanes”

    • Author(s)
      T. Shibata, K. Kanda, R. Hamanaka, K. Endo,
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC)
    • Place of Presentation
      Siem Reap, Combodia
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Application of New Phosphine Ligands Containing Planer-chiral Paracyclophane Skeletons

    • Author(s)
      濵中 理紗、神田 和正, 遠藤 恆平, 柴田 高範
    • Organizer
      Symposium on Molecular Chirality ASIA 2012
    • Place of Presentation
      福岡
    • Related Report
      2012 Annual Research Report
  • [Presentation] 不斉オルトリチオ化を利用した[n]パラシクロファン骨格を有する新規面不斉リン配位子の合成とパラジウム触媒を用いた不斉カップリングへの応用

    • Author(s)
      濵中 理紗・神田 和正・柴田 高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Annual Research Report
  • [Presentation] 不斉薗頭カップリング反応による面不斉を有するパラシクロファンの高エナンチオ選択的合成

    • Author(s)
      大嶋 祥也・濵中 理紗・神田 和正・柴田 高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.waseda.ac.jp/shibata/

    • Related Report
      2012 Final Research Report
  • [Remarks] 柴田研究室HP

    • URL

      http://www.chem.waseda.ac.jp/shibata/

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.waseda.ac.jp/shibata/

    • Related Report
      2011 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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