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Development of the highly efficient iron-catalyzed asymmetric reaction system aimed for the versatile synthesis of chiral compounds of biological interest

Research Project

Project/Area Number 23590011
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKumamoto University

Principal Investigator

MATSUNAGA Hirofumi  熊本大学, 大学院生命科学研究部, 准教授 (10274713)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords鉄 / 触媒 / エポキシ化 / 酸化 / 1,2-ジアミン / キラル合成子 / 生理活性物質 / 配位子 / 不斉配位子
Research Abstract

A new method was established for the preparation of trans-4,5-dimethoxy-2-imidazolidinone (DMIm), versatile chiral synthon for the preparation of various optically active 1,2-diamines which were very useful in the field of pharmaceutical and/or agrochemical science, via the Fe(III)-catalyzed oxidation of 2-imidazolone by H2O2-urea followed by the subsequent optical resolution via the introduction of a MAC moiety. Chiral DMIm was also available from highly diastereoselective Fe-catalyzed oxidation of chiral 2-imidazolone. Enantioselective oxidation of trans-stilbene catalyzed by chiral "roofed" cis-1,2-diamine-iron complex was tried and moderate enantioselectivity was achieved.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (24 results)

All 2014 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (16 results) Remarks (3 results)

  • [Journal Article] HIGHLY EFFICIENT PREPARATION OF BOTH ENANTIOMERS OF VERSATILE CHIRAL SYNTHON FOR 1,2-DIAMINES VIA THE Fe(III)-CATALYZED OXIDATION OF 2-IMIDAZOLONE2014

    • Author(s)
      Hirofumi MATSUNAGA, Iori ESHITA, Shoichi TSUNODA, Naoko ISHIMOTO,Shin ANDO, Tadao ISHIZUKA
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 2 Pages: 1337-1353

    • DOI

      10.3987/com-13-s(s)104

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Study of the Various Factors That Affect the Properties of Molecularly Imprinted Polymers2013

    • Author(s)
      Yasuyama, T.; Matsunaga, H.; Ando, S.; Ishizuka, T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 61 Issue: 5 Pages: 546-550

    • DOI

      10.1248/cpb.c12-01044

    • NAID

      130003360773

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of effectively-shielded N-heterocyclic carbene ligands2013

    • Author(s)
      Ando, S.; Matsunaga, H.; Ishizuka, T.
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 6 Pages: 1687-1693

    • DOI

      10.1016/j.tet.2012.12.036

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] A study of the various factors that affect the properties of Molecularly imprinted polymers2013

    • Author(s)
      Takuro YASUYAMA, Hirofumi MATSUNAGA, Shin ANDO, Tadao ISHIZUKA
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 61

    • NAID

      130003360773

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Simple, Iron-Catalyzed, Pyridine-Assisted Hydrogen Peroxide Epoxidation System2011

    • Author(s)
      Mingyu, J.; Matsunaga, H.; Ishizuka, T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 59 Issue: 6 Pages: 799-801

    • DOI

      10.1248/cpb.59.799

    • NAID

      130000748013

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 配座固定cis-1,2-ジアミンを利用したアミン-チオウレア型触媒の創製と反応2013

    • Author(s)
      松永浩文、田嶋大輔、川内哲郎、安藤眞、石塚忠男
    • Organizer
      第39回反応と合成の進歩シンポジウム講演要旨集
    • Place of Presentation
      九州大学医学部百年講堂 (1P-68 (p.85))
    • Related Report
      2013 Final Research Report
  • [Presentation] ビシクロ環を母核としたキラルカルベン配位子の合成と立体選択的アリル位アリール化反応への応用2013

    • Author(s)
      安藤眞、松永浩文、石塚忠男
    • Organizer
      第39回反応と合成の進歩シンポジウム講演要旨集1
    • Place of Presentation
      九州大学医学部百年講堂 (P-28 (p.45))
    • Related Report
      2013 Final Research Report
  • [Presentation] 鉄触媒酸化反応を利用した1,2-ジアミンキラルシントン両体掌体効率合成法の開発2013

    • Author(s)
      松永浩文、江下伊織、安藤眞、石塚忠男
    • Organizer
      第43回複素環化学討論会講演要旨集
    • Place of Presentation
      長良川国際会議場(1P-04 (p.51))
    • Related Report
      2013 Final Research Report
  • [Presentation] 鉄触媒酸化反応を利用した1,2-ジアミンキラルシントン両体掌体効率合成法の開発2013

    • Author(s)
      松永浩文、江下伊織、安藤 眞、石塚忠男
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Annual Research Report
  • [Presentation] ビシクロ環を母核としたキラルカルベン配位子の合成と立体選択的アリル位アリール化反応 への応用2013

    • Author(s)
      安藤 眞、松永浩文、石塚忠男
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂
    • Related Report
      2013 Annual Research Report
  • [Presentation] 配座固定cis-1,2- ジアミンを利用したアミン- チオウレア型触媒の創製と反応特性2013

    • Author(s)
      松永浩文、田嶋大輔、川内哲郎、安藤 眞、石塚忠男
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部百年講堂
    • Related Report
      2013 Annual Research Report
  • [Presentation] 配座固定cis-アミノチオウレア型有機触媒の創成と反応特性2012

    • Author(s)
      田嶋大輔、川内哲郎、安藤眞、松永浩文、石塚忠男
    • Organizer
      第29回日本薬学会九州支部大会講演要旨集
    • Place of Presentation
      熊本大学薬学部 (1C-03 (p.56))
    • Related Report
      2013 Final Research Report
  • [Presentation] Molecularly imprinted polymerを利用した不斉合成反応の試み2012

    • Author(s)
      安山卓郎、松永浩文、安藤眞、石塚忠男
    • Organizer
      第38回反応と合成の進歩シンポジウム講演要旨集
    • Place of Presentation
      タワーホール船堀 (2P-34 (p.268))
    • Related Report
      2013 Final Research Report
  • [Presentation] 効率的に立体遮蔽された含窒素複素環カルベン配位子の合成と特徴2012

    • Author(s)
      安藤眞、松永浩文、石塚忠男
    • Organizer
      第42回複素環化学討論会講演要旨集
    • Place of Presentation
      京都テルサ (2P-032 (p.149)
    • Related Report
      2013 Final Research Report
  • [Presentation] 鉄触媒酸化反応を利用した1,2-ジアミンキラルシントン合成法の開発2012

    • Author(s)
      江下伊織、松永浩文、石塚忠男
    • Organizer
      日本薬学会第132年会講演要旨集
    • Place of Presentation
      北海道大学 (30P1-pm119)
    • Related Report
      2013 Final Research Report
  • [Presentation] 効率的に立体遮蔽された含窒素複素環カルベン配位子の合成と特徴2012

    • Author(s)
      安藤 眞、松永浩文、石塚忠男
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都テルサ
    • Related Report
      2012 Research-status Report
  • [Presentation] Molecularly imprinted polymer を利用した不斉合成反応の試み2012

    • Author(s)
      安山卓郎、松永浩文、安藤 眞、石塚忠男
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2012 Research-status Report
  • [Presentation] 配座固定cis-アミノチオウレア型有機触媒の創成と反応特性2012

    • Author(s)
      田嶋大輔、川内哲郎、安藤 眞、松永浩文、石塚忠男
    • Organizer
      第29回日本薬学会九州支部大会
    • Place of Presentation
      熊本大学薬学部
    • Related Report
      2012 Research-status Report
  • [Presentation] 不斉酸化反応を用いた1,2-ジアミン類キラルシントン効率合成法の開発と応用2011

    • Author(s)
      江下伊織、松永浩文、石塚忠男
    • Organizer
      第41回複素環化学討論会講演要旨集
    • Place of Presentation
      熊本市民会館 (1P-098 (p.211))
    • Related Report
      2013 Final Research Report
  • [Presentation] 不斉酸化反応を用いた1,2-ジアミン類キラルシントン効率合成法の開発と応用

    • Author(s)
      江下伊織、松永浩文、石塚忠男
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本市民会館
    • Related Report
      2011 Research-status Report
  • [Presentation] 鉄触媒酸化反応を利用した1,2-ジアミンキラルシントン合成法の開発

    • Author(s)
      江下伊織、松永浩文、石塚忠男
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学
    • Related Report
      2011 Research-status Report
  • [Remarks] 創薬基盤分子設計学

    • URL

      http://yakko.pharm.kumamoto-u.ac.jp/

    • Related Report
      2013 Final Research Report
  • [Remarks] 創薬基盤分子設計学

    • URL

      http://yakko.pharm.kumamoto-u.ac.jp/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 創薬基盤分子設計学

    • URL

      http://yakko.pharm.kumamoto-u.ac.jp/

    • Related Report
      2012 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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