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Creation of Novel Asymmetric Catalytic Processes by Biomimetic Multifunctional Molecular Catalysts

Research Project

Project/Area Number 25888012
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

ASANO Keisuke  京都大学, 工学(系)研究科(研究院), 助教 (90711771)

Project Period (FY) 2013-08-30 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords有機分子触媒 / 不斉合成 / アシルアンモニウム / サルファマイケル付加 / ラクトン / 1,5-ベンゾチアゼピン / 複素環合成 / 医薬候補化合物 / 環化付加 / ライブラリー合成 / 二官能性有機分子触媒 / 生体酵素 / 水素結合 / 共有結合性相互作用 / ラクトン合成
Outline of Final Research Achievements

Utilizing α,β-unsaturated acylammonium intermediates generated from carboxylic acid derivatives and tertiary amine catalysts, we accomplished the facile asymmetric syntheses of heterocyclic compounds through the enantioselective introduction of a sulfur atom at the β-position of carboxylic acid derivatives via sulfa-Michael addition. This method enabled the catalytic enantioselective syntheses of β-mercaptolactones and 1,5-benzothiazepines. These heterocycles are highly important as candidates of pharmaceutical agents, and this research can be expected to contribute to the field of drug discovery.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • Research Products

    (33 results)

All 2015 2014 2013 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results,  Acknowledgement Compliant: 3 results) Presentation (22 results) (of which Invited: 1 results)

  • [Journal Article] Facile Net Cycloaddition Approach to Optically Active 1,5-Benzothiazepines2015

    • Author(s)
      Yukihiro Fukata, Keisuke Asano,* and Seijiro Matsubara*
    • Journal Title

      Journal of the American Chemical Society

      Volume: 印刷中 Issue: 16 Pages: 53205323-53205323

    • DOI

      10.1021/jacs.5b02537

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Isomerization of ω-Hydroxy-α,β-Unsaturated Thioesters into β -Mercaptolactones by a Bifunctional Aminothiourea Catalyst2014

    • Author(s)
      Fukata, Y.; Okamura, T.; Asano, K.; Matsubara, S.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 8 Pages: 2184-2187

    • DOI

      10.1021/ol500637x

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] フッ素原子一つで選択性が変わる-新しい合成補助基の提案2014

    • Author(s)
      浅野 圭佑
    • Journal Title

      化学

      Volume: 69 Pages: 64-65

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile2014

    • Author(s)
      Naoki Yoneda, Ayano Hotta, Keisuke Asano,* Seijiro Matsubara*
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 23 Pages: 6264-6266

    • DOI

      10.1021/ol503104b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Chroman Synthesis via an Intramolecular Oxy-Michael Addition by Bifunctional Organocatalysts2014

    • Author(s)
      Ryota Miyaji, Keisuke Asano,* and Seijiro Matsubara*
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 12 Issue: 1 Pages: 119-122

    • DOI

      10.1039/c3ob41938j

    • NAID

      120005526691

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Axially Chiral Compounds by Organocatalysts2014

    • Author(s)
      浅野 圭佑
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 72 Issue: 2 Pages: 185-186

    • DOI

      10.5059/yukigoseikyokaishi.72.185

    • NAID

      130003395386

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 1,3-Oxazolidines via Intramolecular Aza-Michael Addition by Bifunctional Organocatalysts2013

    • Author(s)
      Yukihiro Fukata, Keisuke Asano,* and Seijiro Matsubara*
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 4 Pages: 355-357

    • DOI

      10.1246/cl.121245

    • NAID

      10031162171

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cycloetherifications by Bifunctional Aminothiourea Catalysts: The Importance of Hydrogen Bonding2013

    • Author(s)
      Fukata, Y.; Miyaji, R.; Okamura, T.; Asano, K.; Matsubara, S.
    • Journal Title

      Synthesis

      Volume: 45 Issue: 12 Pages: 1627-1634

    • DOI

      10.1055/s-0032-1316920

    • NAID

      120005474484

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pauson-Khand Reactions in a Photochemical Flow Microreactor2013

    • Author(s)
      Asano, K.; Uesugi, Y.; Yoshida, J.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 10 Pages: 2398-2401

    • DOI

      10.1021/ol4008519

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts2013

    • Author(s)
      Ryota Miyaji, keisuke Asano, Seijiro Matsubara
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 14 Pages: 3658-3661

    • DOI

      10.1021/ol401538b

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts2013

    • Author(s)
      Miyaji, R.; Asano, K.; Matsubara, S.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 33 Pages: 3658-3661

    • DOI

      10.1021/ja407027e

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Facile Cycloaddition Approach to Optically Active 1,5-Benzothiazepines2015

    • Author(s)
      Keisuke Asano,* Yukihiro Fukata, and Seijiro Matsubara*
    • Organizer
      The 39th Naito Conference
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      2015-07-06 – 2015-07-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Axially Chiral Isoquinoline N-Oxides by Bifunctional Organocatalysts2015

    • Author(s)
      Ryota Miyaji, Keisuke Asano,* and Seijiro Matsubara*
    • Organizer
      The 39th Naito Conference
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      2015-07-06 – 2015-07-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 有機触媒による多点活性化が拓く多彩な不斉複素環合成2015

    • Author(s)
      浅野 圭佑
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] キラルリン酸触媒による速度論的分割を伴う不斉1,3-ジオキサン構築2015

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新規有機Lewis塩基触媒の開発を目指した置換トランスシクロオクテンの合成2015

    • Author(s)
      永成 駿介・松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 環化付加による1,5-ベンゾチアゼピンの迅速不斉合成2015

    • Author(s)
      深田 幸宏・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二官能性有機触媒によるシアノヒドリンの不斉分子内オキシマイケル付加反応2015

    • Author(s)
      米田 直紀・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二官能性有機触媒による1,3-ジオールの不斉分子内オキシマイケル付加反応2015

    • Author(s)
      藤井 結稀・米田 直紀・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二官能性有機触媒による軸不斉化合物のエナンチオ選択的合成2015

    • Author(s)
      宮地 亮太・浅野 圭佑・松原 誠二郎
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Isomerization of ω-Hydroxy-α,β- Unsaturated Thioesters into β-Mercaptolactones by Bifunctional Aminothiourea Catalyst2014

    • Author(s)
      Yukihiro Fukata, Takaaki Okamura, Keisuke Asano,* and Seijiro Matsubara*
    • Organizer
      The 9th International Symposium on Integrated Synthesis (ISIS-9)
    • Place of Presentation
      Awaji, Japan
    • Year and Date
      2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Spiroketal Synthesis by Aminothiourea Catalysts2014

    • Author(s)
      Naoki Yoneda, Yukihiro Fukata, Keisuke Asano,* and Seijiro Matsubara*
    • Organizer
      The 9th International Symposium on Integrated Synthesis (ISIS-9)
    • Place of Presentation
      Awaji, Japan
    • Year and Date
      2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Synthesis of 1,3-Dioxanes by Chiral Phosphoric Acid Catalyst2014

    • Author(s)
      Akira Matsumoto, Keisuke Asano,* and Seijiro Matsubara*
    • Organizer
      The 9th International Symposium on Integrated Synthesis (ISIS-9)
    • Place of Presentation
      Awaji, Japan
    • Year and Date
      2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルリン酸触媒による不斉1,3-ジオキサン合成2014

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      東京
    • Year and Date
      2014-10-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] 二官能性有機分子触媒を用いた分子内オキシマイケル 付加反応による不斉クロマン合成2014

    • Author(s)
      宮地 亮太・浅野 圭佑・松原 誠二郎
    • Organizer
      第34回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      大阪大学
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホルムアルデヒドを酸素原子求核剤とする不斉オキシマイケル付加反応2014

    • Author(s)
      堀田 彩乃・米田 直紀・浅野 圭佑・松原 誠二郎
    • Organizer
      第34回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Place of Presentation
      大阪大学
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルリン酸触媒による不斉 1,3-ジオキサン合成反応2014

    • Author(s)
      松本 晃・浅野 圭佑・松原 誠二郎
    • Organizer
      第3回JACI/GSCシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-05-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Procedure-Controlled Enantioselectivity Switch in Organocatalytic 2-Oxazolidinone Synthesis

    • Author(s)
      Keisuke Asano,* Yukihiro Fukata, and Seijiro Matsubara*
    • Organizer
      The Eighth International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Nara
    • Related Report
      2013 Annual Research Report
  • [Presentation] アミノチオウレア触媒によるγ-ヒドロキシ-α,β-不飽和チオエステルの不斉異性化反応

    • Author(s)
      深田幸宏・岡村高明・浅野圭佑・松原誠二郎
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] キラルリン酸触媒による不斉環状エーテル化反応

    • Author(s)
      米田直紀・浅野圭佑・松原誠二郎
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] キラルリン酸触媒による不斉1,3-ジオキサン構築反応

    • Author(s)
      松本晃・浅野圭佑・松原誠二郎
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ホルムアルデヒドを酸素原子求核剤とする不斉オキシマイケル付加反応

    • Author(s)
      堀田彩乃・米田直紀・浅野圭佑・松原誠二郎
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 二官能性有機分子触媒による分子内ヘテロマイケル付加反応を利用したクロマンおよびインドリンの不斉合成

    • Author(s)
      宮地亮太・浅野圭佑・松原誠二郎
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report

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Published: 2013-09-12   Modified: 2019-07-29  

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