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Developments and applications of multifunctional catalytic molecules based on the creation of novel asymmetric reaction space

Research Project

Project/Area Number 21790007
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

NEMOTO Tetsuhiro  Chiba University, 大学院・薬学研究院, 講師 (80361450)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2009: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsジアミノホスフィンオキシド / 触媒的不斉合成 / 有機触媒 / スピロ化合物 / タングトリン / パラジウム / アリル位置換反応 / 水素結合触媒 / 含窒素化合物合成 / 全合成
Research Abstract

The present researches can be summarized as follow. (1) We developed a Pd-catalyzed intramolecular ipso-Friedel-Crafts allylic alkylation of phenols, which provided a new access to spirocyclohexadienones. (2) Novel bidentate-type diaminophosphine oxide preligands were developed and applied to catalytic organic synthesis. In addition, catalytic asymmetric total synthesis of tangutorine was achieved. (3) Novel bifunctional hydrogen bond-donor catalysts based on a 4,5-diaminoxanthene skeleton were developed. These catalysts were applicable to enantioselective conjugate addition of prochiral nucleophiles to nitrostyrenes for constructing an all carbon quaternary stereocenter.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (43 results)

All 2011 2010 2009 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (29 results) Remarks (1 results)

  • [Journal Article] Syntehsis of Novel Bidentate P-Chiral Diaminophosphine Oxide Preligands : Application to Pd-Catalyzed Asymemric Allylic Substitution Reactions.2011

    • Author(s)
      Teusuke Harada, Tetsuhiro Nemoto, Long Jin, Yasumasa Hamada.
    • Journal Title

      Chem.Pharm.Bull. 59

      Pages: 412-415

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel Chiral Hydrogen Bond Donor Catalysts Based on a 4,5-Diaminoxanthene Scaffold : Application to Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes.2011

    • Author(s)
      Tetsuhiro Nemoto, Kazumichi Obuchi, Shinji Tamura, Takashi Fukuyama, Yasumasa Hamada.
    • Journal Title

      Tetrahedron Lett. 52

      Pages: 987-991

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymemtric Synthesis Using P-Chiral Diaminophosphine Oxide Preligands : DIAPHOX.2011

    • Author(s)
      Tetsuhiro Nemoto, Yasumasa Hamada.
    • Journal Title

      Tetrahedron 67

      Pages: 667-687

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel Chiral Hydrogen Bond Donor Catalysts Based on a 4,5-Diaminoxanthene Scaffold : Application to Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes2011

    • Author(s)
      Tetsuhiro Nemoto, Kazumichi Obuchi, Shinji Tamura, Takashi Fukuyama, Yasumasa Hamada
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 987-991

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntehsis of Novel Bidentate P-Chiral Diaminophosphine Oxide Preligands : Application to Pd-Catalyzed Asymemric Allylic Substitution Reactions2011

    • Author(s)
      Teisuke Hazada, Tetsuhiro Nemoto, Long Jin, Yasumasa Hamada
    • Journal Title

      Chem.Pharm.Bull.

      Volume: 59 Pages: 412-415

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis Using P-Chiral Diaminophosphine Oxide Preligands : DIAPHOXs2011

    • Author(s)
      Tetsuhiro Nemoto, Yasumasa Hamada
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 667-687

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] クロスカップリングが切り開いた現代2011

    • Author(s)
      根本哲宏
    • Journal Title

      化学と教育

      Volume: 59 Pages: 96-99

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel Method for Synthesizing Spirocyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols.2010

    • Author(s)
      Tetsuhiro Nemoto, Yuta Ishige, Mariko Yoshida, Yuta Kohno, Mutsumi Kanematsu, Yasumasa Hamada.
    • Journal Title

      Org.Lett. 12

      Pages: 5020-5023

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Total Synthesis of Tangutorine.2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fukamachi, Hiroshi Kobayashi, Yasumasa Hamada.
    • Journal Title

      Org.Lett. 12

      Pages: 872-875

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols2010

    • Author(s)
      Tetsuhiro Nemoto, Yuta Ishige, Mariko Yoshida, Mutsumi Kanematsu, Yuta Kohno, Yasumasa Hamada
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 5020-5023

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Total Synthesis of Tangutorine2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fukamachi, Hiroshi Kobayashi, Yasumasa Hamada
    • Journal Title

      Org.Lett. 12

      Pages: 872-875

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Asymmetric Allylic Alkylation of 2,3-Allenyl Acetates Using a Chiral Diaminophosphine Oxide.2009

    • Author(s)
      Tetsuhiro Nemoto, Mutsumi Kanematsu, Shinji Tamura, Yasumasa Hamada.
    • Journal Title

      Adv.Synth.Catal. 351

      Pages: 1773-1778

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Asymmetric Allylic Alkylation of 2,3-Allenyl Acetates Using a Chiral Diaminophosphine Oxide2009

    • Author(s)
      Tetsuhiro Nemoto, Mutsumi Kanematsu, Shinji Tamura, Yasumasa Hamada
    • Journal Title

      Adv.Synth.Catal. 35

      Pages: 1773-1778

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 有機触媒を用いるγ-ラクタム類の不斉合成2011

    • Author(s)
      横坂卓也、濱嶋祥就、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 分子内Mannich反応を利用したデカヒドロキノリンアルカロイド類の不斉合成研究2011

    • Author(s)
      角河和未、河野優太、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Pd-触媒を用いるフェノール類の分子内イプソ-Friedel-Crafts型アリル位置換反応[2]2011

    • Author(s)
      吉田真理子、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] Pd-触媒を用いるフェノール類の分子内イプソ-Friedel-Crafts型アリル位置換反応[1]2011

    • Author(s)
      石毛裕太、吉田真理子、河野優太、兼松睦、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] Pd-触媒を用いるフェノール類の分子内イプソ-Friedel-Crafts型アリル位置換反応(1)2011

    • Author(s)
      石毛裕太、吉田真理子、河野優太、兼松睦、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Pd-触媒を用いるフェノール類の分子内イプソ-Friedel-Crafts型アリル位置換反応(2)2011

    • Author(s)
      吉田真理子、根本哲宏、濱田康正
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols2010

    • Author(s)
      Tetsuhiro Nemoto, Mariko Yoshida, Yuta Ishige, Mutsumi Kanematsu, Yuta Kohno, Yasumasa Hamada
    • Organizer
      2005 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Novel Method for Synthesizing Spiro[4.5]cyclohexadienones through a Pd-Catalyzed Intramolecular ipso-Friedel-Crafts Allylic Alkylation of Phenols2010

    • Author(s)
      Tetsuhiro Nemoto, Yuta Ishige, Mariko Yoshida, Yuta Kohno, Mutsumi Kanematsu, Yasumasa Hamada
    • Organizer
      The 5^<th> International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Hsinchu, Taiwan
    • Year and Date
      2010-11-09
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] Pd触媒を用いるフェノール類のイプソ-Friedel-Craft型アリル位アルキル化反応:スピロ[4.5]シクロヘキサジエノン類の新規合成法2010

    • Author(s)
      根本哲宏、石毛裕太、吉田真理子、河野優太、兼松睦、濱田康正
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2010-11-02
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 分子内Mannich反応を利用したデカヒドロキノリンアルカロイド類の不斉全合成研究2010

    • Author(s)
      角河和未、根本哲宏、濱田康正
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-14
    • Related Report
      2010 Final Research Report
  • [Presentation] 分子内Mannich 反応を利用したデカヒドロキノリンアルカロイド類の不斉全合成研究2010

    • Author(s)
      角河和未、根本哲宏、濱田康正
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] Chiral Diaminophosphine Oxide (DIAPHOX) Preligand in Organic Synthesis : Catalytic Asymmeric Total Synthesis of Tangutorine2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fukamachi, Hiroshi Kobayashi, Yasumasa Hamada
    • Organizer
      1^<st> Joint Symposium on Pharmaceutical Sciences between College of Pharmacy, Seoul national University and Graduate School of Pharmaceutical Sciences, Chiba University
    • Place of Presentation
      千葉
    • Year and Date
      2010-08-27
    • Related Report
      2010 Final Research Report
  • [Presentation] Chiral Diaminophosphine Oxide (DIAPHOX) Preligand in Organic Synthesis : Catalytic Asymmeric Total Synthesis of Tangutorine2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fukamachi, Hiroshi Kobayashi, Yasumasa Hamada
    • Organizer
      1^<st> Joint Symposium on Pharmaceutical Sciences between College of Pharmacy, Seoul national University and Graduate School of Pharmaceutical Sciences, Chiba University
    • Place of Presentation
      千葉大学
    • Year and Date
      2010-08-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 4,5-ジアミノキサンテン骨格を基盤とするキラル有機触媒の開発2010

    • Author(s)
      小淵和通、田村慎司、福山尚、根本哲宏、濱田康正
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大
    • Year and Date
      2010-05-22
    • Related Report
      2010 Final Research Report
  • [Presentation] 4,5-ジアミノキサンテン骨格を基盤とするキラル有機触媒の開発2010

    • Author(s)
      小淵和通、田村慎司、福山尚、根本哲宏、濱田康正
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大学
    • Year and Date
      2010-05-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] Catalytic Asymmetric Total Synthesis of Tangutorine2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fuakamachi, Hiroshi Kobayashi, Yasumasa Hamada
    • Organizer
      The 21^<st> French-Japanese Synposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2010-05-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Catalytic Asymmetric Total Synthesis of Tangutorine2010

    • Author(s)
      Tetsuhiro Nemoto, Eri Yamamoto, Robert Franzen, Takashi Fukuyama, Riliga Wu, Toshihiko Fuakamachi, Hiroshi Kobayashi, Yasumasa Hamada
    • Organizer
      The 21^<st> French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2010-05-10
    • Related Report
      2010 Annual Research Report
  • [Presentation] エステル共役型キラルシクロヘキセン誘導体へのジアステレオ選択的共役付加反応の開発2010

    • Author(s)
      角河和未、根本哲宏、濱田康正
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] エステル共役型キラルシクロヘキセン誘導体へのジアステレオ選択的共役付加反応の開発2010

    • Author(s)
      角河和未、根本哲宏、濱田康正
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] キサンテン骨格を基盤とするキラル有機触媒の開発と応用2010

    • Author(s)
      小淵和通、田村慎司、福山尚、根本哲宏、濱田康正
    • Organizer
      日本薬学会130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Tangutorineの不斉合成2010

    • Author(s)
      根本哲宏、山本絵理、Robert Franzen, 福山尚、Riliga Wu, 深町利彦、小林弘、濱田康正
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Tangutorine の不斉合成2010

    • Author(s)
      根本哲宏、山本絵理、Robert Franzen,福山尚、 Riliga Wu, 深町利彦、小林弘、濱田康正
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] キサンテン骨格を基盤とするキラル有機触媒の開発と応用2010

    • Author(s)
      小淵和通、田村慎司、福山尚、根本哲宏、濱田康正
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] デカヒドロキノリンアルカロイド類の不斉全合成研究2009

    • Author(s)
      角河和未、福山尚、根本哲宏、濱田康正
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      野田
    • Year and Date
      2009-10-14
    • Related Report
      2010 Final Research Report
  • [Presentation] Chiral Diaminophosphine Oxide (DIAPHOX) Preligand in Organic Synthesis : Catalytic Asymmeric Total Synthesis of Tangutorine2009

    • Author(s)
      Tetsuhiro Nemoto
    • Organizer
      5^<th> Sino-Japanese Symposium on Organic Chemistry for Young Scientists
    • Place of Presentation
      Chengdu, China
    • Year and Date
      2009-10-10
    • Related Report
      2010 Final Research Report
  • [Presentation] Chiral Diaminophosphine Oxide(DIAPHOX)Preligand in Organic Synthesis : Catalytic Asymmeric Total Synthesis of Tangutorine2009

    • Author(s)
      根本哲宏
    • Organizer
      5^<th> Sino-Japanese Symposium on Organic Chemistry for Young Scientists
    • Place of Presentation
      Chengdu, China
    • Year and Date
      2009-10-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Allenes through Asymmetric Allylic Substitution Using a Pd-Chiral Diaminophosphine Oxide Catalyst System2009

    • Author(s)
      Tetsuhiro Nemoto, Mutsumi Kanematsu, Shinji Tamura, Yasumasa Hamada
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学
    • Year and Date
      2009-09-11
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Pd-ジアミノホスフィンオキシド触媒系を用いるアリル位置換反応を利用したアレン類の不斉合成2009

    • Author(s)
      根本哲宏、兼松睦、田村慎司、濱田康正
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      慶応大学薬学部
    • Year and Date
      2009-06-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Pd-ジアミノホスフィンオキシド触媒系を用いるアリル位置換反応を利用したアレン類の不斉合成2009

    • Author(s)
      根本哲宏、兼松睦、田村慎司、濱田康正
    • Organizer
      第95回有機合成シンポジウム
    • Place of Presentation
      慶応大学
    • Year and Date
      2009-06-11
    • Related Report
      2009 Annual Research Report
  • [Remarks] (千葉大学大学院薬学研究院 薬化学研究室)

    • URL

      http://www.p.chiba-u.ac.jp/lab/yakka/index.html

    • Related Report
      2010 Final Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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