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Molecular Design and Synthetic Applications of Chiral Aminophosphonium Salts

Research Project

Project/Area Number 20350018
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

OOI Takashi  Nagoya University, 工学研究科, 教授 (80271708)

Co-Investigator(Kenkyū-buntansha) URAGUCHI Daisuke  名古屋大学, 大学院・工学研究科, 講師 (70426328)
OHMATSU Kohsuke  名古屋大学, 大学院・工学研究科, 助教 (00508997)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥19,370,000 (Direct Cost: ¥14,900,000、Indirect Cost: ¥4,470,000)
Fiscal Year 2010: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2009: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2008: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Keywords有機化学 / 不斉合成 / ホスホニウム塩 / 酸・塩基触媒 / 分子認識
Research Abstract

A series of P-spiro chiral tetraaminophosphonium salts have been designed and synthesized as a new class of organic molecular catalysts, and their inherent abilities to exert four different, synthetically relevant asymmetric catalyses have been brought out through the unique molecular design on a single core structure, N_4P^+. Further, these catalyses have been applied to the development of various C-C, C-P, and C-N bond-forming reactions, in which the remarkably high catalytic performances and stereocontrolling abilities of the chiral tetraaminophosphonium salts have been successfully demonstrated.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (36 results)

All 2011 2010 2009 2008 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (14 results) Book (5 results) Remarks (1 results)

  • [Journal Article] Chiral 1, 2, 3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability : Application to Asymmetric Alkylation of Oxindoles2011

    • Author(s)
      K.Ohmatsu, M.Kiyokawa, T.Ooi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Pages: 1307-1309

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Direct Henry Reaction of Ynals Short Syntheses of (2S,3R)-(+)-Xestoaminol C and (-)-Codonopsinines2010

    • Author(s)
      Uraguchi, D., Nakamura, S., Ooi, T.
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 7562-7565

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton2010

    • Author(s)
      Uraguchi, D., Kinoshita, N.Ooi, T.
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 12240-12242

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Direct Henry Reaction of Ynals : Short Syntheses of (2S, 3R)-(+)-Xestoaminol C and (-)-Codonopsinines2010

    • Author(s)
      D.Uraguchi, S.Nakamura, T.Ooi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 7562-7565

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton2010

    • Author(s)
      D.Uraguchi, N.Kinoshita, T.Ooi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 12240-1242

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Site-directed Asymmetric Quaternization of Peptide Backbone at C-Terminal Azlactone2009

    • Author(s)
      Uraguchi, D., Asai, Y., Ooi, T.
    • Journal Title

      Angew.Chem., Int.Ed. 48

      Pages: 733-737

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of α, α-Disubstituted-α-Amino Acids via Enantioselective Alkylation of Azlactones under Biphasic Conditions Using ρ-Spiro Chiral Tetraaminophosphonium Salts as a Phase-Transfer Catalyst2009

    • Author(s)
      Uraguchi, D., Asai, Y., Seto, Y., Ooi, T.
    • Journal Title

      Synlett

      Pages: 658-660

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive ρ-Nucleophile : Application to Asymmetric Hydrophosphonylation of Aldehydes2009

    • Author(s)
      Uraguchi, D., Ito, T., Ooi, T.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 3836-3837

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Arylaminophosphonium Barfates as a New Class of Charged Bronsted Acid for the Enantioselective Activation of Nonionic Lewis Bases2009

    • Author(s)
      Uraguchi, D., Nakashima, D., Ooi, T.
    • Journal Title

      J.Am.Chem.Soc. 131

      Pages: 7242-7243

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network2009

    • Author(s)
      Uraguchi, D., Ueki, Y., Ooi, T.
    • Journal Title

      Science 326

      Pages: 120-123

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Diastereo-and Enantioselective Direct Henry Reaction of Pyruvates Mediated by Chiral ρ-Spiro Tetraaminophosphonium salts2009

    • Author(s)
      Uraguchi, D., Ito, T., Nakamura, S., Sakaki, S., Ooi, T.
    • Journal Title

      Chem. Lett. 38

      Pages: 1052-1053

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Arylaminophosphonium Barfates as a New Class of Charged Bronsted Acid for the Enantioselective Activation of Nonionic Lewis Bases2009

    • Author(s)
      D.Uraguchi, D.Nakashima, T.Ooi
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 7242-7243

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diastereo- and Enantioselective Direct Henry Reaction of Pyruvates Mediated by Chiral P-Spiro Tetraaminophosphonium salts2009

    • Author(s)
      D.Uraguchi, T.Ito, S.Nakamura, S.Sakaki, T.Ooi
    • Journal Title

      Chemistry Letters 38

      Pages: 1052-1053

    • NAID

      10025547907

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network2009

    • Author(s)
      D.Uraguchi, Y.Ueki, T.Ooi
    • Journal Title

      Science 326

      Pages: 120-123

    • Related Report
      2009 Annual Research Report 2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral Tetraaminophosphonium Chlorides from N-BOC α-Amino Acid Esters2008

    • Author(s)
      Uraguchi D., Sakaki, S., Ueki, Y., Ito, T., OoT.
    • Journal Title

      Heterocycles 76

      Pages: 1081-1085

    • NAID

      40016323216

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Tetraaminophosphonium Carboxylate-Catalyzed Direct Mannich-Type Reaction2008

    • Author(s)
      Uraguchi, D., Ueki, Y., Ooi, T.
    • Journal Title

      J.Am.Chem.Soc. 130

      Pages: 14088-14089

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Presentation] Molecular Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses2010

    • Author(s)
      大井貴史
    • Organizer
      The International Symposia on Advancing the Chemical Sciences 1^<st>(ISACSI) San Francisco
    • Place of Presentation
      USA
    • Year and Date
      2010-07-09
    • Related Report
      2010 Final Research Report
  • [Presentation] Molecular Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses2010

    • Author(s)
      T.Ooi
    • Organizer
      The International Symposia on Advancing the Chemical Sciences 1^<st> (ISACSI)
    • Place of Presentation
      San Francisco, USA
    • Related Report
      2010 Annual Research Report
  • [Presentation] Unique Asymmetric Catalysis of Supramolecularly Assembled Chiral Tetraaminophos honium Phenoxides2010

    • Author(s)
      T.Ooi
    • Organizer
      International Symposium on Organocatalysis Muelheim an der Ruhr ISOμ
    • Place of Presentation
      The Max-Planck-Institut, Muelheim, Germany
    • Related Report
      2010 Annual Research Report
  • [Presentation] Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses2009

    • Author(s)
      大井貴史
    • Organizer
      2009 Workshop on Organometallic Chemistry, Kyushu University
    • Place of Presentation
      Fukuoka
    • Year and Date
      2009-10-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Design of Chiral Tetraaminophosphonium Salts and Their Unique Asymmetric Catalyses2009

    • Author(s)
      大井貴史
    • Organizer
      2009 Workshop on Organometallic Chemistry
    • Place of Presentation
      九州大学 (福岡市)
    • Year and Date
      2009-10-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Molecular Design and Synthetic Applications of Chiral Tetraaminophosphonium Salts2009

    • Author(s)
      大井貴史
    • Organizer
      The 19th Symposium on Optically Active Compounds, Nagai Memorial Hall
    • Place of Presentation
      Tokyo
    • Year and Date
      2009-10-23
    • Related Report
      2010 Final Research Report
  • [Presentation] Molecular Design and Synthetic Applications of Chiral Tetraaminophosphonium Salts2009

    • Author(s)
      大井貴史
    • Organizer
      The 19th Symposium on Optically Active Compounds
    • Place of Presentation
      長井記念ホール(東京都)
    • Year and Date
      2009-10-23
    • Related Report
      2008 Annual Research Report
  • [Presentation] アミノホスホニウム塩の分子設計に基づく触媒機能創出と応用2009

    • Author(s)
      大井貴史
    • Organizer
      理研シンポ.ジウム:第4回「有機合成化学のフロンティア」,理化学研究所, 和光研究所
    • Place of Presentation
      和光
    • Year and Date
      2009-07-03
    • Related Report
      2010 Final Research Report
  • [Presentation] アミノホスホニウム塩の分子設計に基づく触媒機能創出と応用2009

    • Author(s)
      大井貴史
    • Organizer
      理研シンポジウム : 第4回「有機合成化学のフロンティア」
    • Place of Presentation
      理化学研究所 和光研究所 (和光市)
    • Year and Date
      2009-07-03
    • Related Report
      2009 Annual Research Report
  • [Presentation] Design of Chiral Tetraaminophosphonium Salts as an Organic Molecular Catalyst for Selective Chemical Synthesis2009

    • Author(s)
      大井貴史
    • Organizer
      Lecture Tour for Asian Core Program Lectureship Award, Academia Sinica, National Chide Tung University, and National Tsing Hua University, Taipei and Hsinchu
    • Place of Presentation
      Taiwan
    • Related Report
      2010 Final Research Report
  • [Presentation] アミノホスホニウム塩の分子設計に基づく触媒機能創出と不斉合成への活用2008

    • Author(s)
      大井貴史
    • Organizer
      北海道大学グローバルCOEシンポジウム「触媒的不斉合成の最先端」,北海道大学
    • Place of Presentation
      札幌
    • Year and Date
      2008-10-24
    • Related Report
      2010 Final Research Report
  • [Presentation] Toward Asymmetric Synthesis of Oligopeptides Site-Specifically Incorporating Chiral α, α-Dialkyl-α-Amino Acid Residues2008

    • Author(s)
      大井貴史
    • Organizer
      UK/Japan Symposium on Asymmetric Catalysis, Kyoto University
    • Place of Presentation
      Kyoto
    • Related Report
      2010 Final Research Report
  • [Presentation] Molecular Design and Synthetic Utilities of Chiral Organic Ton Pair Catalysts2008

    • Author(s)
      大井貴史
    • Organizer
      5th Annual Japanese-German Frontiers of Science Symposium, Atrium Hotel Mainz
    • Place of Presentation
      Germany
    • Related Report
      2010 Final Research Report
  • [Presentation] Chiral Ammonium Betaines : Design and Application as an Enantioselective Orgainc Base Catalyst2008

    • Author(s)
      大井貴史
    • Organizer
      3rd International Conference on Cutting-Edge Organic Chemistry in Asia under Asian Core Program (ICCEOA-3), Liu Ying Hotel, Hangzhou
    • Place of Presentation
      China
    • Related Report
      2010 Final Research Report
  • [Book] 進盈を紛げる触媒(シンコナアルカロイド型相間移動触媒)(丸岡啓二編)第2部 第2章2009

    • Author(s)
      大井貴史
    • Related Report
      2010 Final Research Report
  • [Book] 進化を続ける有機触媒 第2部 第2章 シンコナアルカロイド型相間移動触媒2009

    • Author(s)
      大井貴史
    • Total Pages
      234
    • Publisher
      化学同人
    • Related Report
      2009 Annual Research Report
  • [Book] 化学(光学活性な炭素の三角形を作る-Corey-ChaykDvsky 反応と親電子剤活性化法の組み合わせ)2008

    • Author(s)
      浦口大輔, 大井貴史
    • Total Pages
      63
    • Related Report
      2010 Final Research Report
  • [Book] WILEY-VCH : Weinheim(Cinchona-derived Chiral Phase-Transfer Catalysts for Amino Acid Synthesis)(In Asymmetric Phase Transfer Catalysis)(Maruoka, K., Ed.)Chapter 22008

    • Author(s)
      大井貴史
    • Related Report
      2010 Final Research Report
  • [Book] WILEY-VCH : Weinheim(Chiral Quaternary Ammonium Fluorides for Asymmetric Synthesis)(In Asymmetric Phase Transfer Catalysis)(Maruoka, K., Ed.)Chapter 92008

    • Author(s)
      Shirakawa, S., Ooi T.; Maruoka, K.
    • Related Report
      2010 Final Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.apehem.nagoya-u.ae.jp/06-II-3/ooiken/Home.html

    • Related Report
      2010 Final Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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