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Fine Design of Bidentate Lewis Acid Catalysts and their Synthetic Application

Research Project

Project/Area Number 19350020
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

MARUOKA Keiji  Kyoto University, 大学院・理学研究科, 教授 (20135304)

Co-Investigator(Kenkyū-buntansha) KANO Taichi  京都大学, 大学院・理学研究科, 講師 (40372560)
HASHIMOTO Takuya  京都大学, 大学院・理学研究科, 助教 (20437198)
Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥18,200,000 (Direct Cost: ¥14,000,000、Indirect Cost: ¥4,200,000)
Fiscal Year 2008: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Fiscal Year 2007: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Keywords触媒的不斉合成 / 二点配位型 / ルイス酸 / ブレンステッド酸 / 有機触媒 / 二点配位型触媒 / 不斉合成 / 精密有機合成化学 / チタン触媒 / イミノアザエナミン反応 / アジリジン化反応 / デザイン / 1,3-双極子環状付加 / シクロプロパン化
Research Abstract

本研究では、次世代の精密有機合成化学への多大な進展に向けて、二点配位型ルイス酸触媒の合理的、合目的な触媒設計を行い、他の反応触媒では及びもつかないような反応性、選択性が獲得できるような、精密合成反応プロセス(触媒的不斉合成も含む)の確立を目指した.その結果、酸素架橋された光学活性チタンルイス酸触媒によるニトロンの1, 3-双極子付加環化反応において、配位子および基質の分子デザインにより、二点配位型ルイス酸触媒に特異的な優れた基質一般性を有する反応系の構築に成功した.また新たな精密ルイス酸触媒の創製では、触媒の活性中心として典型金属や前周期遷移金属のみならず、二つのカルボン酸部位を単一分子内に有する触媒設計に取り組んだ.

Report

(3 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • Research Products

    (29 results)

All 2009 2008 2007 Other

All Journal Article (14 results) (of which Peer Reviewed: 13 results) Presentation (14 results) Remarks (1 results)

  • [Journal Article] Asymmetric 1, 3-Dipolar Cycloadditions of N-Benzyl and N-Diphenylmethyl Nitrones and α , β -Unsaturated Aldehydes Catalyzed by Bis-Titanium Chiral Lewis Acids2008

    • Author(s)
      Hashimoto, T. ; Omote, M. ; Hato, Y. ; Kano, T. ; Maruoka, K.
    • Journal Title

      Chem. Asian J 3

      Pages: 407-412

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] 6, 6'-Substituent Effect of BINOL in Bis-Titanium Chiral Lewis Acid Catalyzed 1, 3-Dipolar Cycloaddition of Nitrones2008

    • Author(s)
      Hashimoto, T. ; Omote, M. ; Maruoka, K.
    • Journal Title

      Org. Biomol. Chem 6

      Pages: 2263-2265

    • Related Report
      2008 Final Research Report
  • [Journal Article] Design of an Axially Chiral Dicarboxylic Acid and Its Application in Syntheses of Optically Active β-Amino Acids and β-Amino Phosphonic Acid Derivatives2008

    • Author(s)
      Hashimoto, T. ; Maruoka, K.
    • Journal Title

      Synthesis

      Pages: 3703-3706

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Imino Aza-enamine Reaction Catalyzed by Axially Chiral Dicarboxylic Acid : Use of Arylaldehyde N, N- ialkylhydrazones as Acyl Anion Equivalent2008

    • Author(s)
      Hashimoto, T. ; Hirose, M. ; Maruoka, K
    • Journal Title

      J. Am. Chem. Soc 130

      Pages: 7556-7557

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid2008

    • Author(s)
      Hashimoto, T. ; Uchiyama, N. ; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc 130

      Pages: 14380-14381

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Manzacidins : A Stage for the Demonstration of Synthetic Methodologies2008

    • Author(s)
      Hashimoto, T. ; Maruoka, K
    • Journal Title

      Org. Biomol. Chem 6

      Pages: 829-835

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric 1.3-Dipolar Cycloadditions of N-Benzyl and N-Diphcnvlmcthyl Niironos and α, β-Unsaturated Aldehydes Catl]yzed by Bis-Titanium Chiral Lewis Acids2008

    • Author(s)
      T. Hashimoto
    • Journal Title

      Chemistry : An Asian Journal 3

      Pages: 407-412

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Imino Aza-enamine Reaction Catalyzed by Axially Chiral Dicarboxylic Acid : Use of Arylaldehyde N, N-Dialkyhydrazoncs as Acyl Anion Equivalent2008

    • Author(s)
      T. Hashimoto
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 7556-7557

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Trans-Selective Asymmetric Aziridination of Diazoacetamides and N-Boc Imines Catalyzed by Axially Chiral Dicarboxylic Acid2008

    • Author(s)
      T. Hashimoto
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 14380-14381

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric 1, 3-Dipolar Cycloadditions of Nitrones and Methacrolein Catalyzed by Chiral Bis-Titanium Lewis Acids : A Dramatic Effect of N-Substituent on Nitrone2007

    • Author(s)
      Hashimoto, T. ; Omote, Kano, T. ; Maruoka, K.
    • Journal Title

      Org. Lett 9

      Pages: 4805-4808

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds2007

    • Author(s)
      Hashimoto, T. ; Maruoka, K.
    • Journal Title

      J. Am. Chem. Soc 129

      Pages: 10054-10055

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Stereodefined 1, 1, 2, 2-Tetrasubstituted Cyclopropanes by Acid Catalyzed Reaction of Aryldiazoacetates and α-Substituted Acroleins2007

    • Author(s)
      T. Hashimoto
    • Journal Title

      Chemical Communications

      Pages: 5143-5145

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of Axially Chiral Dicarboxylic Acid for Asymmetric Mannich Reaction of Arylaldehyde N-Boc Imines and Diazo Compounds2007

    • Author(s)
      T. Hashimoto
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 10054-10055

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric 1, 3-Dipolar Cycloadditions of Nitrones and Methacrolein Catalyzed by Chiral Bis-Titanium Lewis Acids: A Dramatic Effect of N-Substituent on Nitrone2007

    • Author(s)
      T. Hashimoto
    • Journal Title

      Organic Letters 9

      Pages: 4805-4808

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] 軸不斉ジカルボン酸触媒によるジアゾアセトアミドとイミンのトランス選択的不斉アジリジン化反応の開発2009

    • Author(s)
      橋本卓也、内山七瀬、丸岡啓二
    • Organizer
      日本化学会第89春季年会
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Organocatalysts for Catalytic Asymmetric Synthesis2008

    • Author(s)
      Maruoka, K
    • Organizer
      International Workshop on Green Chemistry
    • Place of Presentation
      Hong Kong
    • Year and Date
      2008-04-28
    • Related Report
      2008 Final Research Report
  • [Presentation] 軸不斉ジカルボン酸触媒の創製およびジアゾ化合物の不斉マンニッヒ反応への展開2008

    • Author(s)
      橋本卓也、丸岡啓二
    • Organizer
      日本化学会第88春季年会
    • Related Report
      2008 Final Research Report
  • [Presentation] アザエナミンをアシルアニオン等価体として利用した不斉マンニッヒ反応の開発2008

    • Author(s)
      廣瀬麻野、橋本卓也、丸岡啓二
    • Organizer
      日本化学会第88春季年会
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthetic Utility of Diazoacetates with Chiral Metal and Non-Metal Catalysts2008

    • Author(s)
      Maruoka, K
    • Organizer
      First Japan-Singapore Bilateral Symposium on Catalysis
    • Place of Presentation
      Singapore
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Binaphthyl-Modified Chiral Organocatalysts for Asymmetric Synthesis2008

    • Author(s)
      Maruoka, K
    • Organizer
      9th Netherlands Catalysis and Chemistry Conference
    • Place of Presentation
      Amsterdam, Netherland
    • Related Report
      2008 Final Research Report
  • [Presentation] Organocatalytic Way to the Asymmetric Synthesis of Useful Amino Acids and Alkaloid Derivatives2008

    • Author(s)
      Maruoka, K
    • Organizer
      The 20th French-Japanese Symposium on Medicinal & Fine Chemistry
    • Place of Presentation
      Bordeaux, France
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Axially Chiral Dicarboxylic acid for Asymmetric Mannich-type Reaction2008

    • Author(s)
      Hashimoto, T. ; Maruoka, K
    • Organizer
      20th International Synpossium on Chirality (ISCD20)
    • Place of Presentation
      Geneva, Switzerland
    • Related Report
      2008 Final Research Report
  • [Presentation] Organocatalytic Way to the Asymmetric Synthesis of Useful Amino Acids and Alkaloids2008

    • Author(s)
      K. Maruoka
    • Organizer
      20th International Symposium on Chirality
    • Place of Presentation
      Geneva, Switzerland
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthetic Utility of Diazoacetates with Chiral Metal and Non-Metal Catalysts2008

    • Author(s)
      K. Maruoka
    • Organizer
      First Japan-Singapore Bilateral Symposium on Catalysis
    • Place of Presentation
      National University of Singapor
    • Related Report
      2007 Annual Research Report
  • [Presentation] Designer Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      Gordon Research Conference on Organic Reactions and Processes
    • Place of Presentation
      Rhode Island, U. S. A.
    • Related Report
      2008 Final Research Report
  • [Presentation] Designer Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K
    • Organizer
      The 2nd International Conference on Cutting-Edge Organic Chemsitry
    • Place of Presentation
      Busan, Korea
    • Related Report
      2008 Final Research Report
  • [Presentation] Binaphthyl-Modified Chiral Organocatalysts for Practical Asymmetric Synthesis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      2nd ERA-Chemistry Flash Conference
    • Place of Presentation
      Evora, Portugal
    • Related Report
      2008 Final Research Report
  • [Presentation] Design of Chiral Bifunctional Organocatalysts for Asymmetric Organocatalysis2007

    • Author(s)
      Maruoka, K.
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2007
    • Place of Presentation
      Singapore
    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://kuchem.kyoto-u.ac.jp/yugo/index.html

    • Related Report
      2007 Annual Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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