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Investigation on highly stereoselective preparation of organic molecules by means of photochemical activation

Research Project

Project/Area Number 25410105
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Arai Noriyoshi  北海道大学, 工学(系)研究科(研究院), 准教授 (80282721)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords有機合成化学 / 光反応 / 不斉合成 / 分子触媒 / 立体選択的合成
Outline of Final Research Achievements

It is an important research area to develop new methods for preparation of one of mirror image compounds (chiral compound) selectively. There is growing demand for such technology especially in pharmaceutical chemistry. We investigated on creation of a novel and original molecular photo catalyst, which makes it possible to build up complex compounds hardly accessible by conventional methods. We made a synthetic plan for the photo catalyst starting from readily available commercial chemicals, to succeed in preparation of the novel catalyst. We estimated the performance of the catalyst, to find the catalyst shows acceptable level of selective synthesis of chiral compounds, though there remained room for improvement. We are going to make further progress by modification of the molecular structure of the catalyst.

Report

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

    (13 results)

All 2016 2015 2014 2013 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results,  Open Access: 2 results) Presentation (6 results) (of which Invited: 1 results) Remarks (1 results)

  • [Journal Article] Development of Methods for Construction of Heterocyclic Frameworks by Photochemical Activation of Molecules2016

    • Author(s)
      新井則義,大熊毅
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 4 Pages: 360-371

    • DOI

      10.5059/yukigoseikyokaishi.74.360

    • NAID

      130005150748

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Novel Intramolecular Cyclization-Skeletal Reorganization of 2-Arylthiazoles under Photoirradiation2015

    • Author(s)
      Noriyoshi Arai, Moe Mizota, Takeshi Ohkuma
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 607-616

    • DOI

      10.3987/com-14-s(k)8

    • Related Report
      2015 Annual Research Report 2014 Research-status Report 2013 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Stereoselective Preparation of Spiro[4.4] Cyclic Compounds by the Photochemical Activation of Oxazoles2015

    • Author(s)
      Noriyoshi Arai, Moe Mizota, Takeshi Ohkuma
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 1 Pages: 86-89

    • DOI

      10.1021/ol5032848

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Asymmetric Hydrogenation of Quinoxalines, Benzoxazines, and a Benzothiazine Catalyzed by Chiral Ruthenabicyclic Complexes2013

    • Author(s)
      Noriyoshi Arai, Yu Saruwatari, Kotaro Isobe, Takeshi Ohkuma
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Issue: 14-15 Pages: 2769-2774

    • DOI

      10.1002/adsc.201300604

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehydes with the tol-binap/dbapen/Ruthenium(II) Catalyst2013

    • Author(s)
      Noriyoshi Arai, Keisuke Sato, Keita Azuma, Takeshi Ohkuma
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 29 Pages: 7500-7504

    • DOI

      10.1002/anie.201303423

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Alkynyl Ketones with the η6-Arene/TsDPEN-Ruthenium(II) Catalyst2013

    • Author(s)
      Noriyoshi Arai, Hironori Satoh, Noriyuki Utsumi, Kunihiko Murata, Kunihiko Tsutsumi, Takeshi Ohkuma
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 12 Pages: 3030-3033

    • DOI

      10.1021/ol4012184

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] オキサゾールの光活性化を活用した立体選択的ピロリジジン骨格構築手法の開発検討2016

    • Author(s)
      宇佐見宙樹,新井則義,大熊毅
    • Organizer
      日本化学会北海道支部2016夏季研究発表会
    • Place of Presentation
      室蘭工業大学・室蘭市
    • Year and Date
      2016-07-23
    • Related Report
      2015 Annual Research Report
  • [Presentation] Generation of Molecular Complexity by Photochemical Activation of 5-Membered Heteroaromatics2014

    • Author(s)
      Noriyoshi Arai
    • Organizer
      18th Malaysian International Chemical Congress
    • Place of Presentation
      Putra World Trade Centre (Kuala Lumpur, Malaysia)
    • Year and Date
      2014-11-03 – 2014-11-05
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] オキサゾール類およびチアゾール類の光活性化を利用した新規分子内環化反応2014

    • Author(s)
      溝田 萌・新井 則義・大熊 毅
    • Organizer
      日本化学会北海道支部2014年夏季研究発表会
    • Place of Presentation
      苫小牧工業高等専門学校(苫小牧市)
    • Year and Date
      2014-07-12
    • Related Report
      2014 Research-status Report
  • [Presentation] 光照射による2-アリールチアゾール類の新規分子内環化-骨格組み替え反応

    • Author(s)
      新井則義・溝田 萌・大熊 毅
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Related Report
      2013 Research-status Report
  • [Presentation] オキサゾール類の光活性化を利用した高立体選択的環化反応

    • Author(s)
      溝田 萌・新井則義・大熊 毅
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Related Report
      2013 Research-status Report
  • [Presentation] チオフェン類の光活性化を利用した新規炭素縮環系骨格構築手法の開発

    • Author(s)
      溝田 萌・田中皓一朗・新井則義・大熊 毅
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学(北見市)
    • Related Report
      2013 Research-status Report
  • [Remarks] 北海道大学大学院応用化学部門有機合成化学研究室

    • URL

      http://labs.eng.hokudai.ac.jp/labo/orgsynth/

    • Related Report
      2015 Annual Research Report

URL: 

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

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