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2011 Fiscal Year Final Research Report

Advanced Molecular Transformations by Organ catalysts Based on Molecular Recognition

Research Project

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Project/Area Number 20245021
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

TERADA Masahiro  東北大学, 大学院・理学研究科, 教授 (50217428)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Itaru  東北大学, 大学院・理学研究科, 准教授 (00333899)
MOMIYAMA Norie  東北大学, 大学院・理学研究科, 助教 (80447127)
Project Period (FY) 2008 – 2011
Keywords触媒 / 分子変換 / 不斉合成 / 環境調和 / 水素結合 / 分子認識 / リン酸 / 不斉触媒
Research Abstract

The activation of a substrate by means of a Bronsted acid and base is the most straightforward and common approach used to promote a reaction and hence Bronsted acids and bases have been widely utilized as efficient catalysts for a number of organic transformations. The development of novel Bronsted acid and base catalysts has been continuously studied due to their broad synthetic applicability. In the past decade, innovative research on Bronsted acid catalysis has enabled great progress. Specifically, research has focused on ' chiral Bronsted acid or base catalysis', in which enantioenriched products are obtained using a catalytic amount of a chiral organic molecule bearing an acidic or basic functionality. In our continuous studies on the cultivation of efficient and selective transformations using chiral Bronsted acids and bases, we successfully developed novel chiral Bronsted acids and several enantioselective transformations.

  • Research Products

    (39 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (15 results) (of which Peer Reviewed: 15 results) Presentation (14 results) Book (8 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Relay Catalysis via a Rhodium Complex/Chiral Bronsted Acid Binary System Involving Enantioselective Reduction of a Carbonyl Ylide as the Reactive Intermediate2012

    • Author(s)
      M. Terada, Y. Toda
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Pages: 2093-2097

    • Peer Reviewed
  • [Journal Article] Chiral Bronsted Acid-Catalyzed Stereo selective Addition of Azlactones to 3-Vinylindoles for Facile Access to Enantioenriched Tryptophan Derivatives2011

    • Author(s)
      M. Terada, K. Moriya, K. Kanomata, K. Sorimachi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50 Pages: 12586-12590

    • Peer Reviewed
  • [Journal Article] Design of Chiral Bis-phosphoric Acid Catalyst Derived from (R)-33'-Di(2-hydroxy-3-arylphenyl)binaphthol : Catalytic Enantioselective Diels-Alder Reaction of α, β-Unsaturated Aldehydes with Amidodienes2011

    • Author(s)
      N. Momiyama, T. Konno, T. Furiya, T. Iwamoto, M. Terada
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 19294-19297

    • Peer Reviewed
  • [Journal Article] Direct Enantioselective Amination of α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base2011

    • Author(s)
      M. Terada, K. Amagai, K. Ando, E. Kwon, H. Ube
    • Journal Title

      Chem. Eur. J.

      Volume: 17 Pages: 9037-9041

    • Peer Reviewed
  • [Journal Article] Chiral Bronsted Acid Catalysis for Enantioselective Hosomi-Sakurai Reaction of Imines with Allyltrimethylsilane2011

    • Author(s)
      N. Momiyama, H. Nishimoto, M. Terada
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2126-2129

    • Peer Reviewed
  • [Journal Article] Enantioselective Direct Vinylogous Michael Addition of Functionalized Furanones to Nitroalkenes Catalyzed by an Axially Chiral Guanidine Base2011

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

      Org. Lett

      Volume: 13 Pages: 2026-2029

    • Peer Reviewed
  • [Journal Article] Highly Stereoselective [4+ 2] Cycloaddition of Azlactones to β, γ-Unsaturated .-Ketoesters Catalyzed by an Axially Chiral Guanidine Base2011

    • Author(s)
      M. Terada, H. Nii
    • Journal Title

      Chem. Eur. J.

      Volume: 17 Pages: 1760-1763

    • Peer Reviewed
  • [Journal Article] Asymmetric Direct Vinylogous Aldol Reaction of Furan one Derivatives Catalyzed by an Axially Chiral Guanidine2010

    • Author(s)
      H. Ube, N. Shimada, M. Terada
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 49 Pages: 1858-1861

    • Peer Reviewed
  • [Journal Article] Activation of Hemiaminal Ethers by Chiral Bronsted Acid for Facile Access to Enantioselective Two-Carbon Homologation Using Enecarbamates2009

    • Author(s)
      M. Terada, K. Machioka, K. Sorimachi
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 48 Pages: 2553-2556

    • Peer Reviewed
  • [Journal Article] Chiral Phosphoric Acid Governed anti-Diastereo-and Enantioselective Hetero Diels-Alder Reaction of Glyoxylate2009

    • Author(s)
      N. Momiyama, H. Tabuse, M. Terada
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131 Pages: 12882-12883

    • Peer Reviewed
  • [Journal Article] Double Bond Isomerization/Enantioselective Aza-Petasis-Ferrier Rearrangement Sequence as an Efficient Entry to Anti-and Enantioenriched β-Amino Aldehydes2009

    • Author(s)
      M. Terada, Y. Toda
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131 Pages: 6354-6355

    • Peer Reviewed
  • [Journal Article] Enantioselective Direct Aldol-Type Reaction of Azlactone via Protonation of Vinylether by Chiral Bronsted Acid Catalyst2009

    • Author(s)
      M. Terada, H. Tanaka, K. Sorimachi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 131 Pages: 3430-3431

    • Peer Reviewed
  • [Journal Article] Relay Catalysis by Metal-complex/Bronsted Acid Binary System for Tandem Isomerization/Carbon-Carbon Bond Forming Sequence2008

    • Author(s)
      K. Sorimachi, M. Terada
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130 Pages: 14452-14453

    • Peer Reviewed
  • [Journal Article] Binaphthol-derived Phosphoric Acid as a Versatile Catalyst for Enantioselective Carbon-Carbon Bond Forming Reactions2008

    • Author(s)
      M. Terada
    • Journal Title

      Chem. Commun

      Pages: 4097-4112

    • Peer Reviewed
  • [Journal Article] Enantioselective Activation of Aldehydes by Chiral Phosphoric Acid Catalysts in an Aza-Ene-Type Reaction between Glyoxylate and Enecarbamate2008

    • Author(s)
      M. Terada, K. Soga, N. Momiyama
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 47 Pages: 4122-4125

    • Peer Reviewed
  • [Presentation] Enantioselective Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Phosphoric Acids2012

    • Author(s)
      M. Terada
    • Organizer
      4th Novel Chiral Chemistries Japan 2012
    • Place of Presentation
      Tokyo, Japan
    • Year and Date
      2012-03-15
  • [Presentation] Enantioselective Transformations via Activation of Electron-Rich Double Bonds Using Chiral Phosphoric Acids2011

    • Author(s)
      M. Terada
    • Organizer
      International Symposium of Catalysis and Fine Chemicals 2011
    • Place of Presentation
      Nara, Japan
    • Year and Date
      2011-12-07
  • [Presentation] キラルブレンステッド酸触媒を用いた不斉合成:金属錯体との融合を目指して2011

    • Author(s)
      寺田眞浩
    • Organizer
      第39回オルガノメタリックセミナー<錯体触媒化学のフロンティア>
    • Place of Presentation
      東京工業大学, 東京
    • Year and Date
      2011-11-18
  • [Presentation] Enantioselective Transformations via Activation of Electron-Rich Double Bonds Using Chiral Phosphoric Acids2011

    • Author(s)
      M. Terada
    • Organizer
      First Germany-Japan Organocatalytic Symposium
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2011-10-14
  • [Presentation] Binaphthol-derived Phosphoric Acid as a Versatile Catalyst for Enantioselective Carbon-Carbon Bond Forming Reactions2011

    • Author(s)
      M. Terada
    • Organizer
      3rd UK-Japan Symposium on Catalytic Asymmetric Synthesis
    • Place of Presentation
      Oxford, UK.
    • Year and Date
      2011-04-14
  • [Presentation] Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Carbon-Carbon Bond Forming Reactions2010

    • Author(s)
      M. Terada
    • Organizer
      PACHIFICHEM 2010
    • Place of Presentation
      Hawaii, U. S. A
    • Year and Date
      2010-12-19
  • [Presentation] Binaphthol-derived Phosphoric Acid as a Versatile Catalyst for Enantioselective Carbon-Carbon Bond Forming Reactions2010

    • Author(s)
      M. Terada
    • Organizer
      ACP-ICCEOCA-5/NICCEOCA-1
    • Place of Presentation
      Hsinchu, Taiwan
    • Year and Date
      2010-11-09
  • [Presentation] キラルBronsted酸触媒による不斉炭素-炭素結合生成反応の開発2010

    • Author(s)
      寺田眞浩
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      シーサイドホテル舞子ビラ神戸, 神戸
    • Year and Date
      2010-09-04
  • [Presentation] Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Carbon-Carbon Bond Forming Reactions2010

    • Author(s)
      M. Terada
    • Organizer
      TOCAT6/APCAT5
    • Place of Presentation
      Sapporo
    • Year and Date
      2010-07-21
  • [Presentation] Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Carbon-Carbon Bond Forming Reactions2010

    • Author(s)
      M. Terada
    • Organizer
      International Symposium of Organocatalysts in Mulheim 2010
    • Place of Presentation
      Mulheim an der Ruhr, Germany
    • Year and Date
      2010-07-15
  • [Presentation] Binaphthol-derived Phosphoric Acid as a Versatile Catalyst for Enantioselective Carbon-Carbon Bond Forming Reactions2009

    • Author(s)
      M. Terada
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Seoul, Korea
    • Year and Date
      2009-12-14
  • [Presentation] Enantioselective Direct Aldol-Type Reaction of Azlactone via Protonation of Vinyl Ethers by a Chiral Bronsted Acid Catalyst2009

    • Author(s)
      M. Terada
    • Organizer
      IKCOC11
    • Place of Presentation
      京都
    • Year and Date
      2009-11-11
  • [Presentation] Chiral Bronsted Acid/Base as Versatile Catalysts for Enantioselective Transformations2008

    • Author(s)
      M. Terada
    • Organizer
      Symposium on Optically Active Compounds
    • Place of Presentation
      Tokyo
    • Year and Date
      2008-11-14
  • [Presentation] キラルブレンステッド酸による不斉触媒反応:力量ある有機触媒を目指して2008

    • Author(s)
      寺田眞浩
    • Organizer
      第30回有機化学コロキウム
    • Place of Presentation
      八戸
    • Year and Date
      2008-10-11
  • [Book] Phosphoric Acid Catalysis of Reactions not Involving Imines2012

    • Author(s)
      M. Terada, N. Momiyama
    • Total Pages
      219-278
    • Publisher
      Georg Thieme Verlag KG, New York (K. Maruoka ed.)
  • [Book] Stereoselective Synthesis2011

    • Author(s)
      M. Terada
    • Total Pages
      309-346
    • Publisher
      Thieme, New York (P. A. Evans ed.)
  • [Book] 触媒調整ハンドブック第4編均一系触媒2011

    • Author(s)
      寺田眞浩
    • Total Pages
      397-409
    • Publisher
      (株)エヌ・ティー・エス(監修岩本正和)
  • [Book] Enantioselective Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Phosphoric Acid Catalysts2011

    • Author(s)
      M. Terada
    • Total Pages
      2227-2256
    • Publisher
      Bentham Science Publishers
  • [Book] Axially Chiral Guanidines as an Efficient Bronsted Base Catalyst for Enantioselective Transformations2010

    • Author(s)
      M. Terada
    • Total Pages
      1159-1168
    • Publisher
      J. Synth. Org. Chem. Jpn
  • [Book] Enantioselective Synthesis of Amines by Chiral Bronsted Acid Catalysts-分担2010

    • Author(s)
      M. Terada, N. Momiyama
    • Total Pages
      75-129
    • Publisher
      Wiley-VCH (T. C. Nugent Ed.)
  • [Book] Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Carbon-Carbon Bond Forming Reactions2010

    • Author(s)
      M. Terada
    • Total Pages
      101-119
    • Publisher
      Bull. Chem. Soc. Jpn.
  • [Book] キラルブレンステッド酸触媒-どこまで使いこなせるようになるか-分担2009

    • Author(s)
      寺田眞浩
    • Total Pages
      105-117
    • Publisher
      化学同人(監修丸岡啓二)
  • [Remarks]

    • URL

      http://www.orgreact.sakura.ne.jp/publications/index.html

  • [Patent(Industrial Property Rights)] ビスーリン酸化合物及びそれを用いる不斉反応2011

    • Inventor(s)
      寺田眞浩, 椴山儀恵, 今野徹
    • Industrial Property Rights Holder
      東北大学
    • Industrial Property Number
      出願特許、PCT/JP2011/55296
    • Filing Date
      2011-03-08
    • Overseas

URL: 

Published: 2013-07-31  

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