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Development of Cooperative Catalysis of Chiral Ion Pair

Research Project

Project/Area Number 16H04147
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

Uraguchi Daisuke  名古屋大学, 工学研究科, 准教授 (70426328)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,810,000 (Direct Cost: ¥13,700,000、Indirect Cost: ¥4,110,000)
Fiscal Year 2018: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2017: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2016: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Keywords有機分子触媒 / 有機イオン対 / 選択性 / 不斉合成 / イオン対 / ラジカル / 分岐型反応 / 有機合成化学 / キラル
Outline of Final Research Achievements

A series of chiral ion pair catalysts has been developed for precise regulation of C-C bond formations requiring (multiple) selectivity control. For example, by use of our iminophosphorane catalysts, virtually complete control of regio-, diastereo-, and enantioselectivities was realized in the extended conjugate addition and its diastereoselectivity was successfully reversed through very small modification of the catalyst structure. Development of a chiral non-cordinating anion consisting from phosphorus and tridentate chiral ligands is another remarkable achievement of the program. Furthermore, an intramolecular ion pair having a single-electron transfer ability debuted to the organic molecular catalysis arena during the program period.

Academic Significance and Societal Importance of the Research Achievements

本研究を通して、キラルイオン対触媒により制御できる反応の種類や形式が飛躍的に増えたため、分子レベルのものづくりにおける生産効率が向上した。特に、多くの官能基を含む基質を使いこなし、より複雑な分子を得る上で有効な方法論が提案されたことは、今後の関連分野の発展を刺激するものと期待される。また、本研究で開発された分子触媒のうちのいくつかは史上初の構造をもち、その物性と触媒機能が明らかにされたことは、全く新しい領域を拓く端緒となる成果と位置付けられる。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (37 results)

All 2019 2018 2017 2016

All Journal Article (14 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (17 results) (of which Int'l Joint Research: 4 results,  Invited: 10 results) Book (5 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Chemistry of Ammonium Betaines: Application to Ion-Pair Catalysis for Selective Organic Transformations2018

    • Author(s)
      Uraguchi, Daisuke; Ooi, Takashi
    • Journal Title

      J. Synth. Org. Chem. Jpn.

      Volume: 76 Pages: 1144-1153

    • NAID

      130007503327

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 有機イオン対の触媒化学:構造に由来する機能発現2018

    • Author(s)
      浦口 大輔, 大松 亨介, 大井 貴史
    • Journal Title

      ケミカルタイムズ

      Volume: 00 Pages: 19-25

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Catalyst-Directed Guidance of Sulfur-Substituted Enediolates to Stereoselective Carbon-Carbon Bond Formation with Aldehydes2018

    • Author(s)
      Daisuke Uraguchi, Kohei Yamada, Makoto Sato, and Takashi Ooi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 15 Pages: 5110-5117

    • DOI

      10.1021/jacs.7b12949

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalyst-Enabled Site-divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors2018

    • Author(s)
      Daisuke Uraguchi, Ryo Shibazaki, Naoya Tanaka, Kohei Yamada, Ken Yoshioka, and Takashi Ooi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 17 Pages: 4732-4736

    • DOI

      10.1002/anie.201800057

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Allenedicarboxylate as a Stereochemically Labile Electrophile for Chiral Organic Base-Catalyzed Stereoselective Michael Addition2018

    • Author(s)
      Daisuke Uraguchi, Yasutaka Kawai, Hitoshi Sasaki, Kohei Yamada, and Takashi Ooi
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 4 Pages: 594-597

    • DOI

      10.1246/cl.180031

    • NAID

      130006638890

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion2018

    • Author(s)
      Daisuke Uraguchi, Hitoshi Sasaki, Yuto Kimura, Takaki Ito, and Takashi Ooi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 8 Pages: 2718-2721

    • DOI

      10.1021/jacs.7b13433

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant2017

    • Author(s)
      Tanaka Naoya、Tsutsumi Ryosuke、Uraguchi Daisuke、Ooi Takashi
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 52 Pages: 6999-7002

    • DOI

      10.1039/c7cc02502e

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Unique Site-selectivity Control in Asymmetric Michael Addition of Azlactone to Alkenyl Dienyl Ketones Enabled by P-Spiro Chiral Iminophosphorane Catalysis2017

    • Author(s)
      Ken Yoshioka, Kohei Yamada, Daisuke Uraguchi,Takashi Ooi
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 40 Pages: 5495-5498

    • DOI

      10.1039/c7cc01715d

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles2017

    • Author(s)
      Daisuke Uraguchi, Masahiro Torii, Takashi Ooi
    • Journal Title

      ACS Catal.

      Volume: 7 Issue: 4 Pages: 2765-2769

    • DOI

      10.1021/acscatal.7b00265

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst2017

    • Author(s)
      Daisuke Uraguchi, Ken Yoshioka, Takashi Ooi
    • Journal Title

      Nature Communications

      Volume: 8 Issue: 1 Pages: 14793-14793

    • DOI

      10.1038/ncomms14793

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] [5.5]-<i>P</i>-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones2017

    • Author(s)
      Daisuke Uraguchi, Takaki Ito, Yuto Kimura, Yumiko Nobori, Makoto Sato, Takashi Ooi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 5 Pages: 546-555

    • DOI

      10.1246/bcsj.20170040

    • NAID

      130006770705

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Aza-Henry Reaction of 3-Nitro-Dihydro-2(1H)-Quinolones with N-BOC-Aldimines under the Catalysis of Chiral Ammonium Betaines2017

    • Author(s)
      Daisuke Uraguchi, Masahiro Torii, Kohsuke Kato, Takashi Ooi
    • Journal Title

      Heterocycles

      Volume: 94 Issue: 3 Pages: 441-447

    • DOI

      10.3987/com-16-13642

    • NAID

      40021167541

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study2017

    • Author(s)
      Yamanaka, Masahiro; Sakata, Ken; Yoshioka, Ken; Uraguchi, Daisuke; Ooi, Takashi
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 1 Pages: 541-548

    • DOI

      10.1021/acs.joc.6b02572

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chiral Ammonium Betaine-Catalyzed Asymmetric Mannich-Type Reaction of Oxindoles2017

    • Author(s)
      Masahiro Torii, Kohsuke Kato, Daisuke Uraguchi, and Takashi Ooi
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 12 Pages: 2099-2103

    • DOI

      10.3762/bjoc.12.199

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] P-スピロ型キラルアミノホスホニウム骨格が拓く触媒化学2018

    • Author(s)
      浦口 大輔
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] キラル有機カチオン触媒による多重選択性の同時制御2018

    • Author(s)
      浦口 大輔
    • Organizer
      第13回プロセス化学ラウンジ
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 有機イオンペアが織りなす反応場を使った有機合成2018

    • Author(s)
      浦口 大輔
    • Organizer
      CSJフェスタ2018 フェスタ企画 テーマ企画:これぞ日本が誇る有機合成化学!~多彩な反応から暮らしに役立つ製品開発まで~
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion2018

    • Author(s)
      浦口 大輔
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] キラルアンモニウムベタインを触媒とするジヒドロキノリノンの立体選択的Mannich型反応2017

    • Author(s)
      加藤 康介, 鳥居 雅弘, 浦口 大輔, 大井 貴史
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development and Theoretical Analysis of Catalytic Asymmetric Glycolate Aldol Reaction via Intramolecular Acyl Migration Process2017

    • Author(s)
      Kohei Yamada, Makoto Sato, Daisuke Uraguchi, Takashi Ooi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] キラルイミノホスホランの特性を活かしたアルケニルジエニルケトンに対する1,6-選択的マイケル付加反応の開発2017

    • Author(s)
      吉岡 謙, 浦口 大輔, 大井 貴史
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] デザイン型有機イオン対の触媒化学2017

    • Author(s)
      浦口 大輔
    • Organizer
      有機合成2月セミナー 有機合成のニュートレンド2017
    • Place of Presentation
      大阪
    • Year and Date
      2017-02-01
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 多官能性分子の合成戦略:P-スピロ型アミノホスホニウムイオンによる多重選択性制御2017

    • Author(s)
      浦口 大輔
    • Organizer
      第35回メディシナルケミストリーシンポジウム(MCS2017)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] キラル有機イオン対の触媒化学2017

    • Author(s)
      浦口 大輔
    • Organizer
      第2回分子性触媒若手セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Betaine-Type Electron-Transfer Catalyst: Design and Application2017

    • Author(s)
      浦口 大輔
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] キラルアンモニウムベタインを触媒とするジヒドロキノリノンの立体選択的Mannich型反応2016

    • Author(s)
      加藤 康介, 鳥居 雅弘, 浦口 大輔, 大井 貴史
    • Organizer
      第9回 有機触媒シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2016-12-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 反応性カチオン種の制御を志向した新規キラル非配位性アニオン型触媒の創製と機能2016

    • Author(s)
      佐々木 仁嗣, 浦口 大輔, 大井 貴史
    • Organizer
      第6回 CSJ化学フェスタ
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] N-スルホニルα-イミノエステル由来オキサジリジンの触媒的不斉合成およびキラル酸化剤としての機能評価2016

    • Author(s)
      田中 直也, 浦口 大輔, 大井 貴史
    • Organizer
      第47回 中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋
    • Year and Date
      2016-11-05
    • Related Report
      2016 Annual Research Report
  • [Presentation] Stereoselective Mannich-type Reaction of Oxindoles under the Catalysis of Chiral Ammonium Betaines2016

    • Author(s)
      Kohsuke Kato, Masahiro Torii, Daisuke Uraguchi, Takashi Ooi
    • Organizer
      20th International Symposium on Homogeneous Catalysis 2016
    • Place of Presentation
      京都
    • Year and Date
      2016-07-10
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly Stereoselective Transformations under the Catalysis of P-Spiro Chiral Tetraaminophosphonium Salts2016

    • Author(s)
      Daisuke Uraguchi
    • Organizer
      21st International Conference on Organic Synthesis (ICOS21)
    • Place of Presentation
      Mumbai, India
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] デザイン型有機イオンの力を活かした触媒化学2016

    • Author(s)
      浦口 大輔
    • Organizer
      CSJフェスタ2016 コラボレーション企画 文科省科研費 新学術領域研究「有機分子触媒」特別企画:有機分子触媒による未来型分子変換
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Book] “Molecular Technology: Synthesis Innovation, Volume 4” H. Yamamoto and T. Kato Eds.2019

    • Author(s)
      Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi
    • Publisher
      Wiley-VCH
    • Related Report
      2018 Annual Research Report
  • [Book] 有機分子触媒の開発と工業利用2018

    • Author(s)
      大松 亨介, 浦口 大輔, 大井 貴史
    • Publisher
      シーエムシー出版
    • Related Report
      2018 Annual Research Report
  • [Book] 有機分子触媒の開発と工業利用「多機能型キラルオニウム塩の設計に基づく高選択的分子変換」2018

    • Author(s)
      大松 亨介, 浦口 大輔, 大井 貴史
    • Total Pages
      333
    • Publisher
      シーエムシー出版
    • ISBN
      9784781313238
    • Related Report
      2017 Annual Research Report
  • [Book] CSJカレントレビュー「有機分子触媒の化学」イオン対を中心とした不斉塩基触媒2016

    • Author(s)
      浦口 大輔, 大井 貴史
    • Publisher
      日本化学会
    • Related Report
      2016 Annual Research Report
  • [Book] 「Topics in Current Chemistry: Site Selective Catalysis」Site-Selective Conjugate Addition through Catalytic Generation of Ion-Pairing Intermediates2016

    • Author(s)
      Daisuke Uraguchi, Takashi Ooi
    • Publisher
      Springer
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] キラルボラート塩及びその製造方法2018

    • Inventor(s)
      大井貴史、浦口大輔
    • Industrial Property Rights Holder
      名古屋大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-221395
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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