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Development of Novel Chiral Nucleophilic Catalyst Possessing Triazadiphosphole Structure and Its Application to Enantioselective Acylation

Research Project

Project/Area Number 25810057
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Kondoh Azusa  東北大学, 理学(系)研究科(研究院), 助教 (30645544)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機分子触媒 / トリアザジホスホール / 不斉有機塩基触媒 / 二官能性触媒 / 不斉有機強塩基触媒 / 複素環骨格構築 / ホスファゼン / 有機塩基触媒 / 求核触媒
Outline of Final Research Achievements

With the aim of developing a novel nucleophilic catalyst possessing both of a stereogenic center and a hydrogen-bond donor cite at the position adjacent to the nucleophilic cite, a 1,2,4-triazadiphosphole catalyst was designed and investigated. As a result, we achieved the short-step construction of the triazadiphosphole framework. The catalytic activity of the triazadiphosphole thus synthesized was evaluated, and the compound was found to function as an organobase although the application as a nucleophilic catalystwas not succeeded. After the revision of catalyst structure, a novel bifunctional chiral strong organobase catalyst, which has a quaternary ammonium moiety as a hydrogen-bond donor, was designed and synthesized. The application of the catalyst to some reactions suggested that the quaternary ammonium moiety could effectively serve as a hydrogen-bond donor and involve the stereocontrol of the reactions.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (19 results)

All 2016 2015 2014 2013 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results,  Acknowledgement Compliant: 5 results,  Open Access: 2 results) Presentation (8 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ2016

    • Author(s)
      Azusa Kondoh, Yusuke Ota, Takazumi Komuro, Fuyuki Egawa, Kyohei Kanomata and Masahiro Terada
    • Journal Title

      Chem. Sci.

      Volume: 7 Issue: 2 Pages: 1057-1062

    • DOI

      10.1039/c5sc03175c

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Bronsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement2015

    • Author(s)
      Azusa Kondoh, Masahiro Terada
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 2 Issue: 7 Pages: 801-805

    • DOI

      10.1039/c5qo00108k

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Phenanthrene Derivatives by Intramolecular Cyclization Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Bronsted Base2015

    • Author(s)
      Azusa Kondoh, Takuma Aoki, Masahiro Terada
    • Journal Title

      Chemistry A European Journal

      Volume: 21 Issue: 36 Pages: 12577-12580

    • DOI

      10.1002/chem.201501377

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring Expansion of Epoxides under Bronsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines2015

    • Author(s)
      Azusa Kondoh, Kenta Odaira, Masahiro Terada
    • Journal Title

      Angewandte Chemie International Eddition

      Volume: 54 Issue: 38 Pages: 11240-11244

    • DOI

      10.1002/anie.201505893

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase2015

    • Author(s)
      Azusa Kondoh, Masafumi Oishi, Tadahiro Takeda, Masahiro Terada
    • Journal Title

      Angewandte Chemie International Eddition

      Volume: 54 Issue: 52 Pages: 15836-15839

    • DOI

      10.1002/anie.201508178

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Intermediary P3 Phosphazenium Framework and Its Derivatization to Chiral Cationic Macrocycles Including Two P3 Phosphazenium Units with Hydrogen Bond Donor Sites2015

    • Author(s)
      Masahiro Terada, Kengo Goto, Takashi Ikehara, Azusa Kondoh
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 2 Pages: 1396-1404

    • DOI

      10.3987/com-14-s(k)98

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Kinetic Resolution of Racemic Amino Alcohols through Intermolecular Acetalization Catalyzed by Chiral Brønsted Acid2015

    • Author(s)
      Takuto Yamanaka, Azusa Kondoh, Masahiro Terada
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 3 Pages: 1048-1051

    • DOI

      10.1021/ja512238n

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base2014

    • Author(s)
      Azusa Kondoh, Takuma Aoki, Masahiro Terada
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 13 Pages: 3528-3531

    • DOI

      10.1021/ol501479t

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Brønsted Base Catalyzed [2,3]-Wittig/Phospha-Brook Tandem Rearrangement Sequence2013

    • Author(s)
      A. Kondoh, M. Terada
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 17 Pages: 4568-4571

    • DOI

      10.1021/ol402144q

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Phosphazene-Catalyzed Intramolecular Cyclization of Nitrogen-Tethered Alkynyl Esters2013

    • Author(s)
      A. Kondoh, K. Ando, M. Terada
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 87 Pages: 10254-10256

    • DOI

      10.1039/c3cc46100a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Design and Synthesis of Helically Chiral Spirocyclic P3 Phosphazenes and Characterization of Their Onium Salts2013

    • Author(s)
      M. Terada, K. Goto, M. Oishi, T. Takeda, E. Kwon, A. Kondoh
    • Journal Title

      Synlett

      Volume: 24 Issue: 19 Pages: 2531-2534

    • DOI

      10.1055/s-0033-1340058

    • Related Report
      2013 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Bronsted Base-Catalyzed Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines2015

    • Author(s)
      Azusa Kondoh, Kenta Odaira, Masahiro Terada
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      The Hawaii Convention Center
    • Year and Date
      2015-12-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of highly active bifunctional organocatalyst having quaternary ammonium as a key functional group2015

    • Author(s)
      Katsunori Dan, Azusa Kondoh, Masahiro Terada
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      The Hawaii Convention CenterD
    • Year and Date
      2015-12-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Bronsted Base-Catalyzed Intramolecular Cyclization Utilizing [1,2]-Phospha-Brook Rearrangement2015

    • Author(s)
      Azusa Kondoh, Takuma Aoki, Masahiro Terada
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2015-11-12
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Brønsted Base-Catalyzed Three Component Reaction Utilizing [1,2]-Phospha-Brook Rearrangement2015

    • Author(s)
      Azusa Kondoh, Masahiro Terada
    • Organizer
      日本化学会第95年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス/薬学部
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] ブレンステッド塩基触媒を用いた[2,3]-Wittig/Phospha-Brook連続転位反応2014

    • Author(s)
      近藤 梓、寺田 眞浩
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内北キャンパス
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Presentation] 塩基触媒によるPhospha-Brook転位を利用したカルボニル化合物のα位酸素官能基化反応2014

    • Author(s)
      近藤 梓、寺田 眞浩
    • Organizer
      「有機分子触媒による未来型分子変換」第4回公開シンポジウム
    • Place of Presentation
      北海道大学 学術交流会館
    • Year and Date
      2014-06-20
    • Related Report
      2014 Research-status Report
  • [Presentation] Base-Catalyzed [2,3]-Wittig/Phospha-Brook Tandem Rearrangement Sequence

    • Author(s)
      Azusa Kondoh, Masahiro Terada
    • Organizer
      第1回 国際会議 (兼) 第6回 有機触媒シンポジウム
    • Place of Presentation
      大津プリンスホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] 塩基触媒によるPhospha-Brook 転位を利用したカルボニル化合物のα位酸素官能基化反応

    • Author(s)
      近藤 梓、寺田 眞浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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