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Synthesis of planar chiral polyaromatic compounds and application to the asymmetric catalysis

Research Project

Project/Area Number 24590006
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMeijo University

Principal Investigator

KITAGAKI Shinji  名城大学, 薬学部, 教授 (20281818)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機化学 / パラシクロファン / 有機分子触媒 / 不斉配位子 / 面不斉 / [2.2]パラシクロファン / ビスオキサゾリン配位子 / チオウレア触媒 / 合成化学 / ホスフィン触媒 / 酸-塩基複合型不斉触媒
Outline of Final Research Achievements

The [2.2]paracyclophane (PCP)-based planar-chiral organocatalysts and ligands, 1) which had functional group(s) through the spacer aryl group or 2) which were designed for regio- or stereoselectivity control based on the π-π, CH-π, or cation-π interaction, were synthesized and evaluated. Among PCP organocatalysts and ligands tested, the catalyst whose phosphine unit is connected with a cyclopanol via a spacer benzene ring and C2-symmetric bis(oxazoline) ligands having the spacer with a sterically demanding substituent were found to catalyze organic transformations with high enantiocontrol.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (11 results)

All 2015 2014 2013 2012

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (7 results)

  • [Journal Article] Synthesis of planar chiral [2.2]paracyclophane-based bisoxazoline ligands bearing no central chirality and application to Cu-catalyzed asymmetric O-H insertion reaction2015

    • Author(s)
      S. Kitagaki, K. Sugisaka, C. Mukai
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 17 Pages: 4833-4836

    • DOI

      10.1039/c5ob00452g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [2+2+1] Cyclization in allenes2014

    • Author(s)
      S. Kitagaki, F. Inagaki, C. Mukai
    • Journal Title

      Chem. Soc. Rev.

      Volume: 43 Issue: 9 Pages: 2956-2978

    • DOI

      10.1039/c3cs60382b

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Planar chiral [2.2]paracyclophane-based phosphine-Bronsted acid catalysts bearing exceptionally high reactivity for aza-Morita-Baylis-Hillman reaction2013

    • Author(s)
      S. Kitagaki
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Issue: 5 Pages: 384-386

    • DOI

      10.1016/j.tetlet.2012.11.021

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Planar Chiral [2.2]Paracyclophane-based Bis(thiourea) Catalyst: Application to Asymmetric Henry Reaction.2013

    • Author(s)
      Kitagaki, S.
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 38 Pages: 4030-4032

    • DOI

      10.1039/c3cc41789a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] [2.2]パラシクロファンを基本骨格とする面不斉ビスオキサゾリン-銅触媒を 用いたフェノール性O-H挿入反応2015

    • Author(s)
      北垣伸治、浅岡希咲、武永尚子、杉坂健太、向 智里
    • Organizer
      日本薬学会135年会
    • Place of Presentation
      神戸学院大学(兵庫)
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] [2.2]パラシクロファン骨格を有する面不斉ホスフィン-フェノール触媒:不斉アザ-Morita-Baylis-Hillman反応への適用2014

    • Author(s)
      北垣伸治、安達早紀、太田有羽、武永尚子、向 智里
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      東北大学(宮城)
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] シクロファン骨格を有する面不斉ホスフィン触媒を用いた アザ-Morita-Baylis-Hillman反応2014

    • Author(s)
      北垣伸治、安達早紀、太田有羽、武永尚子、向 智里
    • Organizer
      第60回日本薬学会東海支部総会・大会
    • Place of Presentation
      鈴鹿医療科学大学(三重)
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] [2.2]パラシクロファンを基本骨格とする面不斉ビスチオウレアの合成と各種酸触媒反応への適用2014

    • Author(s)
      北垣伸治、安藤美沙紀、上田崇宏、向 智里
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Research-status Report
  • [Presentation] [2.2]パラシクロファン骨格を有する面不斉ビスチオウレア触媒:不斉ニトロアルドール反応への適用2013

    • Author(s)
      北垣伸治、上田崇宏、向 智里
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学(福岡)
    • Related Report
      2013 Research-status Report
  • [Presentation] 面不斉[2.2]パラシクロファニルホスフィン触媒の合成とアザ-Morita-Baylis-Hillman反応への適用2013

    • Author(s)
      北垣伸治
    • Organizer
      日本薬学会133年会
    • Place of Presentation
      パシフィコ横浜(神奈川)
    • Related Report
      2012 Research-status Report
  • [Presentation] 面不斉[2.2]パラシクロファン含有ビスオキサゾリン/銅錯体によるX-H挿入反応2012

    • Author(s)
      杉坂健太
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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