• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

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

Research Project

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
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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.

Report

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

    (54 results)

All 2014 2013 2012 2011 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (37 results) (of which Invited: 2 results) Book (1 results) Remarks (7 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Rh-Catalyzed Direct Enantioselective Alkynylation of α-Ketiminoesters.2013

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

      Chem. Eur. J.

      Volume: 19 Issue: 26 Pages: 8417-8417

    • DOI

      10.1002/chem.201301237

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Microwave-Assisted Deacylation of Unactivated Amides Using Ammonium-Salt-Accelerated Transamidation2012

    • Author(s)
      Yuhei Shimizu, Hiroyuki Morimoto, Ming Zhang and Takashi Ohshima*
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 51 Issue: 34 Pages: 8564-8567

    • DOI

      10.1002/anie.201202354

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] 安定なアミド結合を温和に切断!--強酸、強塩基を必要としないアミド切断反応2012

    • Author(s)
      清水 悠平、森本 浩之、大嶋 孝志
    • Journal Title

      化学(化学同人)

      Volume: 67 Pages: 70-71

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Alkynylation of Imines that Enables the Construction of Tetrasubstituted Carbon Stereocenters2012

    • Author(s)
      Hiroyuki Morimoto
    • Journal Title

      Farumashia

      Volume: 48 Pages: 329-329

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides2011

    • Author(s)
      Hiroyuki Morimoto, Tetsu Tsubogo, Nichole D. Litvinas and John F. Hartwig
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 50 Issue: 16 Pages: 3793-3798

    • DOI

      10.1002/anie.201100633

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereodivergent Direct Catalytic Asymmetric Mannich-type Reaction of α-Isothiocyanato Ester with Ketimines2011

    • Author(s)
      Lu, G.; Yoshino, T.; Morimoto, H.; Matsunaga, S.; Shibasaki, M.
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 50 Issue: 19 Pages: 4382-4385

    • DOI

      10.1002/anie.201101034

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 化合物ライブラリー構築を指向した環境調和型触媒反応の開発2014

    • Author(s)
      森本浩之
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本 熊本大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 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2014

    • 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
      日本薬学会第134年会
    • Place of Presentation
      熊本 熊本大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] αーケトおよびケチ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反応機構解析2014

    • 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
      日本薬学会第134年会
    • Place of Presentation
      熊本 熊本大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ロジウム触媒によるα-ケチ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及びメカニズム解析2014

    • 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105回有機合成シンポジウム【春】
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Presentation] Rh-Catalysed Direct Enantioselective Alkynylation of α-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
      長崎市
    • Related Report
      2013 Annual Research Report
  • [Presentation] Rh-Catalysed Direct Enantioselective Alkynylation of α-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
    • Related Report
      2013 Annual Research Report
  • [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
      福岡市 九州大学百年講堂
    • Related Report
      2013 Annual Research Report
  • [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50回化学関連支部合同九州大会
    • Place of Presentation
      小倉 北九州国際会議場
    • Related Report
      2013 Annual Research Report
  • [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 宮城蔵王ロイヤルホテル
    • Related Report
      2013 Annual Research Report
  • [Presentation] Rh-Catalyzed Direct Enantioselective Alkylation of α-Ketoiminoesters2013

    • Author(s)
      Takashi Ohshima, Kazushiro 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
      Fort Collins, Colorado, USA
    • Related Report
      2013 Annual Research Report
  • [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
    • Place of Presentation
      岡山
    • Related Report
      2013 Annual Research Report
  • [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 九州大学医学部百年記念講堂
    • Related Report
      2013 Annual Research Report
  • [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 長崎国際大学
    • Related Report
      2013 Annual Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Presentation] Rh-Catalyzed Direct Catalytic Asymmetric Alkynylation of α-Ketiminoesters2012

    • Author(s)
      Kazuhiro Morisaki, Jun-ya Nomaguchi, Hiroyuki Morimoto, Yousuke Takeuchi, Takahito Kawabata, Kazushi Mashima, Takashi Ohshima
    • Organizer
      The 132nd Annual Meeting of the Pharmaceutical Society of Japan
    • Place of Presentation
      北海道大学、札幌
    • Related Report
      2011 Research-status Report
  • [Presentation] General, Copper-Mediated Trifluoromethylation of Aryl Iodides Under Mild Conditions2011

    • Author(s)
      Hiroyuki Morimoto, Tetsu Tsubogo, Nichole D. Litvinas, John F. Hartwig
    • Organizer
      The 58th Symposium on Organometallic Chemistry
    • Place of Presentation
      名古屋大学、名古屋
    • Related Report
      2011 Research-status Report
  • [Presentation] General, Copper-Mediated Trifluoromethylation of Aryl Iodides Under Mild Conditions2011

    • Author(s)
      Hiroyuki Morimoto, Tetsu Tsubogo, Nichole D. Litvinas, John F. Hartwig
    • Organizer
      The 9th Symposium on Organic Chemistry-The Next Generation-
    • Place of Presentation
      日本薬学会長井記念館、澁谷、東京
    • Related Report
      2011 Research-status Report
  • [Presentation] Amide Bond Cleavage via Transamidation: Ammonium-Salt-Accelerated Deacylation of Unactivated Amides.

    • Author(s)
      Hiroyuki Morimoto, Yuhei Shimizu, Megumi Noshita, Ming Zhang, Takashi Ohshima
    • Organizer
      10th Seminar of Department of Pharmaceutical Sciences for Young Researchers
    • Place of Presentation
      九州大学、福岡
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Amide Bond Cleavage via Transamidation: Ammonium-Salt-Accelerated Deacylation of Unactivated Amides

    • Author(s)
      Hiroyuki Morimoto, Yuhei Shimizu, Megumi Noshita, Ming Zhang, Takashi Ohshima
    • Organizer
      The 6th Takeda Science Foundation Symposium on PharmaSceinces
    • Place of Presentation
      武田薬品工業(株)研修所、大阪
    • Related Report
      2012 Research-status Report
  • [Presentation] Stable Amide Bond Cleavage Under Mild Conditions

    • Author(s)
      Hiroyuki Morimoto, Yuhei Shimizu, Megumi Noshita, Ming Zhang, Takashi Ohshima
    • Organizer
      12th Systematic Research Core for Drug Development
    • Place of Presentation
      九州大学、福岡
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Lanthanum Trifluoromethanesulfonate-Catalyzed Amidation of Esters with Amines

    • Author(s)
      Hiroyuki Morimoto, Risa Fujiwara, Yuhei Shimizu, Kazuhiro Morisaki, Takashi Ohshima
    • Organizer
      The 133rd Annual Meeting of the Pharmaceutical Society of Japan
    • Place of Presentation
      パシフィコ横浜、神奈川
    • Related Report
      2012 Research-status Report
  • [Presentation] Lanthanum Triflate-Catalyzed Direct Amidation of Esters with Amines

    • Author(s)
      Hiroyuki Morimoto, Risa Fujiwara, Yuhei Shimizu, Kazuhiro Morisaki, Takashi Ohshima
    • Organizer
      The 23rd French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      ANAクラウンプラザホテル長崎グラバーヒル、長崎
    • Related Report
      2012 Research-status Report
  • [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
    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2013 Final Research Report
  • [Remarks] 森本 浩之  助教

    • URL

      http://green.phar.kyushu-u.ac.jp/member/morimoto.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 九州大学-研究者情報 [森本 浩之 (助教) 薬学研究院 臨床薬学部門]

    • URL

      http://hyoka.ofc.kyushu-u.ac.jp/search/details/K003794/index.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 森本浩之 助教

    • URL

      http://green.phar.kyushu-u.ac.jp/member/morimoto.html

    • Related Report
      2012 Research-status Report
  • [Remarks] 九州大学ー研究者情報[森本浩之(助教) 薬学研究院 臨床薬学部門]

    • URL

      http://hyoka.ofc.kyushu-u.ac.jp/search/details/K003794/index.html

    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://green.phar.kyushu-u.ac.jp/member/morimoto.html

    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://hyoka.ofc.kyushu-u.ac.jp/search/details/K003794/index.html

    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] アミノ基および/または水酸基を有する化合物の製造方法2012

    • Inventor(s)
      大嶋孝志、森本浩之、清水悠平
    • Industrial Property Rights Holder
      大嶋孝志、森本浩之、清水悠平
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-12-03
    • Related Report
      2012 Research-status Report
  • [Patent(Industrial Property Rights)] 脱CO方法2012

    • Inventor(s)
      大嶋孝志、森本浩之、清水悠平
    • Industrial Property Rights Holder
      大嶋孝志、森本浩之、清水悠平
    • Industrial Property Number
      2012-046588
    • Filing Date
      2012
    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] G2/M期停止及び細胞死を誘導するベンゾヒドラジド誘導体2011

    • Inventor(s)
      藤田雅俊、大嶋孝志、森本浩之
    • Industrial Property Rights Holder
      藤田雅俊、大嶋孝志、森本浩之
    • Industrial Property Number
      2011-234309
    • Filing Date
      2011
    • Related Report
      2011 Research-status Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi