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Development of chiral picolinic acid-type ligand and application for saymmetric catalysis

Research Project

Project/Area Number 25410112
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

TANAKA Shinji  名古屋大学, 物質科学国際研究センター, 助教 (00529034)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsピリジン-2-カルボン酸 / 光学活性配位子 / 不斉アリル化 / アトロープ異性 / 脱水反応 / ルテニウム / ラクトン / ピコリン酸 / ヘテロ環 / ピリジン
Outline of Final Research Achievements

Picolinic acid (pyridine-2-carboxylic acid) is a well known as chelating ligand and more than ten-thousands related complexes has been reported. On the other hand, the number of the reports concerning about extension for catalytic reactions is less, especially in asymmetric reactions. In this work, to present a potential of the picolinic acid for the transition-metal catalysis, we have aimed to construct the library of the chiral ligands, and investigated about optical stability through comparison with the stabilities of their corresponding benzoic acid derivatives. We have established catalytic asymmetric dehydrative intramolecular allylation of carboxylic acids to give alkenyl lactones, which is difficult to be realized by convensional Tsuji-Trost allylation.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (15 results)

All 2015 2014 2013

All Journal Article (9 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results) Presentation (6 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results)

  • [Journal Article] Stereochemical Stability Differences between Axially Chiral 6-Aryl-substituted Picolinic Esters and Their Benzoic Ester Derivatives: sp2N: vs sp2CH in CH3, C6H5, and CH3O ortho-Substitution Effect,2015

    • Author(s)
      Tanaka, S.; Suzuki, Y.; Matsushita, M.; Kitamura, M.
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Pages: 1726-1734

    • NAID

      130005113802

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 'Intramolecular Tsuji-Trost-type Allylation of Carboxylic Acids: Asymmetric Synthesis of Highly π-Allyl Donative Lactones2015

    • Author(s)
      Suzuki, Y.; Seki, T.; Tanaka, S.; Kitamura, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Pages: 9539-9542

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Mechanism of Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by a Combined System of Ru(π-CH2C(CH3)CH2)2(cod) and the Chiral sp2N/sp3NH Hybrid Linear N4 Ligand Ph-BINAN-H-Py2015

    • Author(s)
      Nakatsuka, H.; Yamamura, T.; Shuto, Y.; Tanaka, S.; Yoshimura, M.; Kitamura, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Pages: 8138-8149

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Soft Ruthenium and Hard Bronsted Acid Combined Catalyst for Efficient Cleavage of Allyloxy Bonds. Application to Protecting Group Chemistry,2015

    • Author(s)
      Tanaka, S.; Suzuki, Y.; Saburi, H.; Kitamura, M.
    • Journal Title

      Tetrahedron

      Volume: 71 Pages: 6559-6568

    • Related Report
      2015 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Donor-Acceptor Bifunctional Molecular Catalyst: Its Development, Application, and Analysis2015

    • Author(s)
      Kitamura, M.; Tanaka, S.; Yoshimura, M.
    • Journal Title

      J. Synth. Org. Chem., Jpn.

      Volume: 73 Pages: 690-700

    • NAID

      130005093742

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Asymmetric NaBH₄ 1,4-Reduction of C(3)-Disubstituted 2-Propenoates Catalyzed by a Diamidine Cobalt Complex2015

    • Author(s)
      Shuto, Y.; Yamamura, T.; Tanaka, S.; Yoshimura, M.; Kitamura, M.
    • Journal Title

      ChemCatChem

      Volume: 000 Pages: 000-000

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Recent topics in catalytic asymmetric hydrogenation of ketones2014

    • Author(s)
      Yoshimura, M.; Tanaka, S.; Kitamura, M.
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 27 Pages: 3635-3640

    • DOI

      10.1016/j.tetlet.2014.04.129

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of tert-Alkyl Ketones: DMSO Effect in Unification of Stereoisomeric Ruthenium Complexes2013

    • Author(s)
      Tomoya Yamamura, Hiroshi Nakatsuka, Shinji Tanaka, Masato Kitamura
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 35 Pages: 9313-9315

    • DOI

      10.1002/anie.201304408

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] CpRu-catalyzed asymmetric dehydrative allylation2013

    • Author(s)
      Masato Kitamura, Kengo Miyata, Tomoaki Seki, Namdev Vatmurge, Shinji Tanaka
    • Journal Title

      Pure and Applied Chemistry

      Volume: 85 Issue: 6 Pages: 1121-1132

    • DOI

      10.1351/pac-con-12-10-02

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Soft Ruthenium and Hard Bronsted Acid Combined Catalyst for Efficient Cleavage of Allyloxy Bonds toward Protecting Chemistry,2015

    • Author(s)
      Tanaka, S.; Suzuki, Y.; Saburi, H.; Kitamura, M.
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ハワイ
    • Year and Date
      2015-12-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Asymmetric Synthesis of Saturated Heterocyclic Compounds via Dehydrative Tsuji-Trost Reaction2014

    • Author(s)
      Tanaka, S.; Kitamura, M.
    • Organizer
      Vietnam Malaysia International Chemical Congress
    • Place of Presentation
      Hanoi
    • Year and Date
      2014-11-07
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] DMSO Effect for Unification of Ruthenium Complex Bearing Linear Tridentate PNN Ligand in Asymmetric Hydrogenation of Functionalized and Unfunctionalized tert-Alkyl Ketones2014

    • Author(s)
      Tanaka, S.; Yamamura, T.; Kitamura, M.
    • Organizer
      The 18th Malaysian International Chemical Congress
    • Place of Presentation
      Kuala Lumpur
    • Year and Date
      2014-11-04
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] CpRu¬¬-Catalyzed Dehydrative Allylation of Thiols and Application for Peptide Modification2014

    • Author(s)
      Tanaka, S.; Kitamura, M.
    • Organizer
      XXVI International Conference on Organic Chemistry
    • Place of Presentation
      Sapporo
    • Year and Date
      2014-07-17
    • Related Report
      2014 Research-status Report
  • [Presentation] Catalytic Dehydrative S-Allylation of Cysteine-Containing Peptide2014

    • Author(s)
      Tanaka, S.; Kitamura, M.
    • Organizer
      The 4th International Conference on MEXT Project of Integrated Research on Chemical Synthesis
    • Place of Presentation
      Kyoto
    • Year and Date
      2014-07-14
    • Related Report
      2014 Research-status Report
  • [Presentation] Development of Magnetically Separable Heterogeneous Deallylation Catalyst2013

    • Author(s)
      Tanaka, S.; Kitamura, M.
    • Organizer
      The 16th International Symposiumon Relations Between Homogeneous ond Heterogeneous Catalysis
    • Place of Presentation
      Sapporo
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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