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Proactive utilization of aqueous environments to explore organic reactions

Research Project

Project/Area Number 15H06134
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Kitanosono Taku  東京大学, 大学院理学系研究科(理学部), 特任助教 (50755981)

Project Period (FY) 2015-08-28 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords水 / 反応場 / 触媒 / 溶媒 / 有機合成 / 不斉 / 界面活性剤 / 不溶 / 水中特異的 / 不斉反応 / ミセル / 環境調和 / 人工触媒 / 酵素
Outline of Final Research Achievements

The purpose of this research aims to substantiate the potentiality of "in water" to achieve novel modes of chemical transformations that may be difficult or sluggish to perform in organic solvents. Subsequently, the superiority of water over organic solvents was displayed in several asymmetric reactions. Besides, multidisciplinary studies led to profound insights fundamentally to explore this field. The outcomes of this research would make significant contributions to synthetic chemistry as well as to minimize the ecological footprint of organic chemistry, causing a drastic paradigm shift of chemical synthesis from “in organic solvent” to “in water”.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • Research Products

    (26 results)

All 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results,  Open Access: 3 results) Presentation (17 results) (of which Int'l Joint Research: 8 results) Remarks (2 results)

  • [Int'l Joint Research] University of Basel/ETH Zurich(スイス)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Upregulation of an Artificial Zymogen by Proteolysis2016

    • Author(s)
      Z. Liu, V. Lebrun, T. Kitanosono, H. Mallin, V. Kohler, D. Haussinger, D. Hilvert, S. Kobayashi, T. R. Ward
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 38 Pages: 11587-11590

    • DOI

      10.1002/anie.201605010

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Surfactant-aided chiral palladium(II) catalysis exerted exclusively in water for the C-H functionalization of indoles2016

    • Author(s)
      T. Kitanosono, M. Miyo, S. Kobayashi
    • Journal Title

      ACS Sustainable Chem. Eng.

      Volume: 4 Issue: 11 Pages: 6101-6106

    • DOI

      10.1021/acssuschemeng.6b01519

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The combined use of cationic palladium(II) with a surfactant for the C-H functionalization of indoles and pyrroles in water2015

    • Author(s)
      T. Kitanosono, M. Miyo, S. Kobayashi
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 40 Pages: 7739-7744

    • DOI

      10.1016/j.tet.2015.07.044

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The Mechanism of Iron(II)-catalyzed Asymmetric Mukaiyama Aldol Reaction in Aqueous Media: Den-sity Functional Theory and Artificial Force-Induced Reaction Study2015

    • Author(s)
      W.M.C. Sameera, M. Hatanaka, T. Kitanosono, S. Kobayashi, K. Morokuma
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 34 Pages: 11085-11094

    • DOI

      10.1021/jacs.5b05835

    • NAID

      120005672549

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chiral Cu(II)-Catalyzed Enantioselective β-Borylation of α,β-Unsaturated Nitriles in Water2015

    • Author(s)
      L. Zhu, T. Kitanosono, P. Xu, S. Kobayashi
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 11 Pages: 2007-2011

    • DOI

      10.3762/bjoc.11.217

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] An Insoluble Copper(II) Acetylacetonate-Chiral Bipyridine Complex that Catalyzes Asymmetric Silyl Conjugate Addition in Water2015

    • Author(s)
      T. Kitanosono, L. Zhu, C. Liu, P. Xu, S. Kobayashi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 49 Pages: 15422-15425

    • DOI

      10.1021/jacs.5b11418

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Development of Novel LASC-SWNT Catalysts and Their Applications Toward Asymmetric Reactions in Water2017

    • Author(s)
      P. Xu, T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] Oxidation of Active Methylene Compounds in Water2017

    • Author(s)
      T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] 水中でのパラジウム触媒による3-メチルインドールのsp3炭素におけるC-H変換反応2017

    • Author(s)
      M. Miyo, T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] 固定化キラル2,2'-ビピリジン配位子を用いたエナンチオ選択的ルイス酸触媒反応の開発2017

    • Author(s)
      K. Masuda, T. Kitanosono, L. Zhu, S. Kobayashi
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Surfactant-aided chiral catalysis for C-H bond functionalization of indoles in water2016

    • Author(s)
      T. Kitanosono, M. Miyo, S. Kobayashi
    • Organizer
      The 8th Green Solvents Conference
    • Place of Presentation
      キール(ドイツ)
    • Year and Date
      2016-10-19
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly Efficient Asymmetric Mukaiyama Aldol Reactions in Water2016

    • Author(s)
      L. Zhu, T. Kitanosono, S. Kobayashi
    • Organizer
      Symposium on Frontiers of Molecular Science and Technology
    • Place of Presentation
      東京大学(東京都文京区)
    • Year and Date
      2016-07-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 水中におけるケイ素の不斉共役付加反応の開発2016

    • Author(s)
      徐鵬宇、劉暢、朱磊、北之園拓、小林修
    • Organizer
      第109回有機合成シンポジウム
    • Place of Presentation
      東京工業大学(東京都目黒区)
    • Year and Date
      2016-06-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis and Application of Immobilized Chiral 2,2'-Bipyridine Ligand2016

    • Author(s)
      L. Zhu, T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of Hydration Reactions in Water with New Photo-Harvesting Catalysts2016

    • Author(s)
      P. Xu, T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Exploration of asymmetric reactions in water using water-insoluble chiral catalysts2016

    • Author(s)
      T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Chiral Palladium(II)-catalyzed Asymmetric 1,4-Addition Reactions of Indoles in Water2016

    • Author(s)
      M. Miyo, T. Kitanosono, S. Kobayashi
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] Chiral Copper(II) Catalysis for Enantioselective Silyl Conjugate Additions in Water [口頭発表]2015

    • Author(s)
      T. Kitanosono, L. Zhu, C. Liu, P. Xu, S. Kobayashi
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイ州ホノルル(米国)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Catalytic Construction of Hydrogen Isotope Chirality in Deuterium Oxide2015

    • Author(s)
      T. Kitanosono, S. Kobayashi
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイ州ホノルル(米国)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Asymmetric Mukaiyama Aldol Reactions Without Use of Organic Solvent2015

    • Author(s)
      L. Zhu, T. Kitanosono, S. Kobayashi
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイ州ホノルル(米国)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design of Novel Catalysts in Water Utilizing Interaction between Lewis Acid-Surfactant-Combined Catalyst and Single-Walled Carbon Nanotube2015

    • Author(s)
      P. Xu, T. Kitanosono, S. Kobayashi
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイ州ホノルル(米国)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Palladium-Catalyst Mixed with Surfactant for Michael Reactions in Water2015

    • Author(s)
      M. Miyo, T. Kitanosono, S. Kobayashi
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイ州ホノルル(米国)
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Chiral Cu(II)-Catalyzed Asymmetric Silyl Conjugate Additions in Water2015

    • Author(s)
      L. Zhu, T. Kitanosono, C. Liu, P. Xu, S. Kobayashi
    • Organizer
      15th Tateshina Conference on Organic Chemistry
    • Place of Presentation
      蓼科フォーラム(長野県茅野市)
    • Year and Date
      2015-11-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Remarks] 東京大学大学院理学系研究科化学専攻有機化学研究室ホームページ

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/synorg/index.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] プレスリリース

    • URL

      http://www.s.u-tokyo.ac.jp/ja/press/2015/58.html

    • Related Report
      2015 Annual Research Report

URL: 

Published: 2015-08-26   Modified: 2018-03-22  

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