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2013 Fiscal Year Final Research Report

Development of catalytic asymmetric addition reactions via direct nucleophilic activation of unactivated C-H bonds

Research Project

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Project/Area Number 23790014
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKyushu University

Principal Investigator

MORIMOTO Hiroyuki  九州大学, 薬学研究科(研究院), 助教 (20593867)

Project Period (FY) 2011 – 2013
Keywords炭素ー水素結合活性化 / 遷移金属触媒 / 不斉反応 / アルキニル化 / 環境調和型反応 / アミノ酸誘導体 / 不斉四置換炭素構築
Research Abstract

Throughout this study, we developed direct catalytic asymmetric addition reactions via nucleophilic C-H bond activation, and we succeeded in obtaining alpha-amino acid derivatives containing chiral tetrasubstituted carbon stereocenters under proton-transfer conditions. The reactions proceed at or below room temperature, and various acid- and base-sensitive functionalities are tolerant under the reaction conditions.
We also performed detailed mechanistic analysis of the reaction and isolated catalytically active species. This active species enabled shortening reaction time and performing reactions with other less-reactive substrates to provide alpha-amino acid derivatives containing chiral tetrasubstituted carbon stereocenters.

  • Research Products

    (19 results)

All 2013 2012 Other

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

  • [Journal Article] Rh-Catalyzed Direct Enantioselective Alkynylation ofα-Ketiminoesters2013

    • Author(s)
      Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima
    • Journal Title

      Chem. Eur. J

      Volume: 19 Pages: 8417

    • DOI

      10.1002/chem.201301237.

    • Peer Reviewed
  • [Presentation] α-ケトイミノエステルに対する直接的触媒的不斉アルキニル化反応の開発2013

    • Author(s)
      澤真尚,森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第30回日本薬学会九州支部大会
    • Place of Presentation
      長崎
    • Year and Date
      2013-12-07
  • [Presentation] ロジウム触媒を用いたケチミンに対する直接的触媒的不斉アルキニル化反応の開発2013

    • Author(s)
      澤真尚,森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Year and Date
      2013-11-05
  • [Presentation] α-ケトイミノエステルの直接的触媒的不斉アルキニル化反応の開発2013

    • Author(s)
      澤真尚,森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第30回有機合成化学セミナー
    • Year and Date
      2013-09-18
  • [Presentation] Rh-Catalyzed Direct Enantioselective Alkylation ofα-Ketoiminoesters2013

    • Author(s)
      Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima
    • Organizer
      17th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS17)
    • Place of Presentation
      Colorado, USA
    • Year and Date
      2013-07-29
  • [Presentation] ロジウム触媒によるα-ケトイミノエステルの直接的不斉アルキニル化反応の開発2013

    • Author(s)
      森崎一宏,澤真尚,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第46回有機金属若手の会夏の学校
    • Place of Presentation
      宮城
    • Year and Date
      2013-07-09
  • [Presentation] ロジウム触媒によるα-ケトイミノエステルの直接的不斉アルキニル化反応の開発2013

    • Author(s)
      森崎一宏,澤真尚,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第23回万有福岡シンポジウム
    • Place of Presentation
      福岡
    • Year and Date
      2013-06-01
  • [Presentation] Rh-Catalysed Direct Enantioselective Alkynylation ofα-Ketiminoesters2013

    • Author(s)
      Takashi Ohshima, Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima
    • Organizer
      Thieme Nagoya Symposium
    • Place of Presentation
      名古屋
    • Year and Date
      2013-05-23
  • [Presentation] Rh-Catalysed Direct Enantioselective Alkynylation ofα-Ketiminoesters2013

    • Author(s)
      Kazuhiro Morisaki, Masanao Sawa, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima, Takashi Ohshima
    • Organizer
      Twenty-third French-Japanese Symposium on Medicinal and Fine Chemistry (FJS-2013)
    • Place of Presentation
      長崎
    • Year and Date
      2013-05-13
  • [Presentation] α-ケトイミノエステルの直接的触媒的不斉アルキニル化反応の開発2013

    • Author(s)
      森崎一宏,澤真尚,野間口順哉,森本浩之,竹内洋介,真島和志
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      2013-03-30
  • [Presentation] ロジウム触媒によるα-ケトイミノエステルの直接的不斉アルキニル化反応2012

    • Author(s)
      森崎一宏,野間口順哉,澤真尚,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第29回日本薬学会九州支部大会
    • Place of Presentation
      熊本
    • Year and Date
      2012-12-08
  • [Presentation] Rh-Catalyzed Direct Asymmetric Alkynylation ofα-Ketoiminoesters2012

    • Author(s)
      Kazuhiro Morisaki, Jun-ya Nomaguchi, Masanao Sawa, Hiroyuki Morimoto, Yosuke Takeuchi, Kazushi Mashima
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2012-09-14
  • [Presentation] ロジウム触媒によるα-ケトイミノエステルの直接的不斉アルキニル化反応の開発2012

    • Author(s)
      森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第29回有機合成化学セミナー
    • Place of Presentation
      静岡
    • Year and Date
      2012-09-06
  • [Presentation] Rh-Phebox-Catalyzed Asymmetric Alkynylation ofα-Ketoesters andα-Ketoiminoesters2012

    • Author(s)
      Takashi Ohshima, Kazuhiro Morisaki, Jun-ya Nomaguchi, Hiroyuki Morimoto, Takahito Kawabata, Yosuke Takeuchi, Kazushi Mashima
    • Organizer
      13th Beligian Organic Synthesis Symposium BOSS 2012
    • Place of Presentation
      Leuven, Belgium
    • Year and Date
      2012-07-19
  • [Presentation] ロジウム触媒によるαーケトイミノエステルの直接的触媒的不斉アルキニル化反応の開発2012

    • Author(s)
      森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      第49回化学関連支部合同九州大会
    • Place of Presentation
      小倉
    • Year and Date
      2012-06-30
  • [Presentation] ロジウム触媒を用いたαーケトイミノエステルの直接的触媒的不斉アルキニル化反応の開発2012

    • Author(s)
      森崎一宏,野間口順哉,森本浩之,竹内洋介,真島和志,大嶋孝志
    • Organizer
      Symposium on Molecular Chirality ASIA 2012 (MCASIA2012)
    • Place of Presentation
      福岡
    • Year and Date
      2012-05-17
  • [Presentation] ロジウム触媒を用いたα-ケトイミノエステルの直接的触媒的不斉アルキニル化反応の開発2012

    • Author(s)
      森崎一宏,野間口順哉,森本浩之,竹内洋介,川端崇仁,真島和志,大嶋孝志
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道
    • Year and Date
      2012-03-30
  • [Book] 四置換炭素構築を可能とするイミンの直接的触媒的不斉アルキニル化ファルマシア2012

    • Author(s)
      森本浩之
    • Total Pages
      48,329
  • [Remarks]

    • URL

      http://green.phar.kyushu-u.ac.jp/

URL: 

Published: 2015-06-25  

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