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Development of helicenyl phosphines and their application in catalytic asymmetric reactions

Research Project

Project/Area Number 16K18846
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Usui Kazuteru  九州大学, 薬学研究院, 助教 (80553304)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords不斉合成 / キラリティー / ヘリセン / らせん / ホスフィン配位子 / 不斉触媒反応 / 有機化学 / 螺旋
Outline of Final Research Achievements

A series of novel optically active [5]helicene-derived phosphine ligands (L1, with a 7,8-dihydro[5]helicene core structure, and L2, with a fully aromatic [5]helicene core structure) were synthesized. The prepared ligands, especially L1, were found to be highly effective in asymmetric allylation of 1,3-diphenylallyl acetate with indoles (up to 99% ee) and etherification with alcohols (up to 96% ee). In asymmetric Suzuki-Miyaura coupling reaction, L2 shown excellent enantioselectivities (up to 99% ee).

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (43 results)

All 2018 2017 2016 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 2 results,  Open Access: 1 results) Presentation (27 results) (of which Int'l Joint Research: 3 results,  Invited: 4 results) Remarks (4 results)

  • [Journal Article] Thienyl-Substituted α-Ketoamide: A Less Hydrophobic Reactive Group for Photo-Affinity Labeling2018

    • Author(s)
      Ota Eisuke、Usui Kazuteru、Oonuma Kana、Koshino Hiroyuki、Nishiyama Shigeru、Hirai Go、Sodeoka Mikiko
    • Journal Title

      ACS Chemical Biology

      Volume: 13 Issue: 4 Pages: 876-880

    • DOI

      10.1021/acschembio.7b00988

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium-periodate mediated harringtonine derivatives and their antiproliferative activity against HL-60 acute leukemia cells2018

    • Author(s)
      Sakamoto, S., Miyamoto, T., Usui, K., Tanaka, H., Morimoto, S.
    • Journal Title

      Journal of Natural Products

      Volume: 81 Issue: 1 Pages: 34-40

    • DOI

      10.1021/acs.jnatprod.7b00541

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of New Chiral Phosphine Ligands with Helical Environments and Their Application in Asymmetric Catalytic Reactions2017

    • Author(s)
      Kazuteru Usui
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 137 Issue: 11 Pages: 1381-1390

    • DOI

      10.1248/yakushi.17-00151

    • NAID

      130006191253

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2017-11-01
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 7-Hydroxy-3-methyleneisoindolin-1-one as a New ESIPT-Fluorescent Probe to Monitor Aqueous Environments2017

    • Author(s)
      Yusuke Kimuro, Kazuteru Usui, Satoru Karasawa, Go Hirai, Mariko Aso
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 8 Pages: 796-800

    • DOI

      10.1248/cpb.c17-00306

    • NAID

      130005875867

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Water-Proton Relaxivities of Radical Nanoparticles Self-Assembled via Hydration or Dehydration Processes2017

    • Author(s)
      Kosuke Morishita, Yuna Okamoto, Shuhei Murayama, Kazuteru Usui, Eriko Ohashi, Go Hirai, Ichio Aoki, Satoru Karasawa
    • Journal Title

      Langmuir

      Volume: 33 Issue: 31 Pages: 7810-7817

    • DOI

      10.1021/acs.langmuir.7b01126

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-step transformation of p-anisolylaminoquinoline derivatives induced by conformation- and packing-dominated processes2017

    • Author(s)
      Ryusuke Hagihara, Kazuteru Usui, Satoru Karasawa
    • Journal Title

      Dyes and Pigments

      Volume: 143 Pages: 401-408

    • DOI

      10.1016/j.dyepig.2017.04.063

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sodium periodate-mediated conjugation of harringtonine enabling the production of a highly specific monoclonal antibody, and the development of a sensitive quantitative analysis method2017

    • Author(s)
      Seiichi Sakamoto*, Gorawit Yusakul, Yumi Tsuneura, Waraporn Putalun, Kazuteru Usui,Tomofumi Miyamoto, Hiroyuki Tanaka, Satoshi Morimoto*
    • Journal Title

      Analyst

      Volume: 142 Issue: 7 Pages: 1140-1148

    • DOI

      10.1039/c6an02751b

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Self-Assembly Behavior of Emissive Urea Benzene Derivatives Enables Heat-Induced Accumulation in Tumor Tissue2017

    • Author(s)
      Takeru Araki, Shuhei Murayama, Kazuteru Usui, Takashi Shimada, Ichio Aoki, and Satoru Karasawa
    • Journal Title

      Nano Lett.

      Volume: 17 Issue: 4 Pages: 2397-2403

    • DOI

      10.1021/acs.nanolett.6b05371

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rational Design and Synthesis of [5]Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions2016

    • Author(s)
      Kosuke Yamamoto, Takashi Shimizu, Kazunobu Igawa, Katsuhiko Tomooka, Go Hirai, Hiroshi Suemune, and Kazuteru Usui
    • Journal Title

      Scientific Reports

      Volume: 6 Issue: 1 Pages: 36211-36211

    • DOI

      10.1038/srep36211

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Electron Paramagnetic Resonance Studies of Oligodeoxynucleotides Containing 2-N-tert-Butylaminoxyl-2’-deoxyadenosines2016

    • Author(s)
      Manami Kurita, Yoshitaka Higuchi, JW Mirc, Shintaro Matsumoto, Kauteru Usui, Hiroshi Suemune, Mariko Aso*
    • Journal Title

      ChemBioChem

      Volume: 17 Issue: 24 Pages: 1-8

    • DOI

      10.1002/cbic.201600465

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Site-specific turn-on fluorescent labeling of DNA-interacting protein using oligo- deoxynucleotides that modify lysines to produce 5,6-dimethoxy-3-methylene- isoindolin-1-one2016

    • Author(s)
      C. Gatanaga, B. Yang, Y. Inadomi, K. Ueda, K. Usui, T. Katayama, H. Suemune, and M. Aso
    • Journal Title

      ACS Chem. Biol.

      Volume: 11 Issue: 8 Pages: 2216-2221

    • DOI

      10.1021/acschembio.6b00090

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Photocyclizations of Di(quinolinyl)arylamines and Tri(quinolinyl)amine with Emission Color Changes and Photoreaction-induced Self-assemblies2016

    • Author(s)
      Satoru Karasawa, Jun-ichi Todo, Kazuteru Usui, Naomi Harada, Kenji Yoza, Hiroshi Suemune and Noboru Koga
    • Journal Title

      Chem E-J.

      Volume: in press Issue: 23 Pages: 7771-7781

    • DOI

      10.1002/chem.201600514

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthetic studies of C-linked disaccharide analogues based on radical coupling2018

    • Author(s)
      Yu Hidaka, Noriaki Kiya, Kazuteru Usui, Go Hirai
    • Organizer
      IRCCS-JST CREST Joint Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Challenges for synthesis of C-glycosides using glycosyl radicals2018

    • Author(s)
      Kazuteru Usui
    • Organizer
      KU-NTU Joint International Symposium on Pharmaceutical Sciences Supported by Kyushu University World Premier International Researcher Invitation Program "Progress 100"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 還元的クロスカップリング反応によるアリール C-グリコシドの合成研究2018

    • Author(s)
      臼井一晃、長門石昌孝、郭義天、平井剛
    • Organizer
      日本薬学会 第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ラジカルカップリング反応を基盤とする炭素連結型2 糖アナログの合成研究2018

    • Author(s)
      木谷憲昭、日高悠、臼井一晃、平井剛
    • Organizer
      日本薬学会 第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高い緩和能を有する超分子型 MRI 造影剤の構築2018

    • Author(s)
      唐澤悟、荒木健、嶋田敬志、臼井一晃、平井剛
    • Organizer
      日本薬学会 第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 過ヨウ素酸ナトリウムによるハリントニン誘導体の作出及びヒト前骨髄性白血病細胞 HL60 に対する増殖阻害活性2018

    • Author(s)
      坂本政一、宮本智文、臼井一晃、田中宏幸、森元聡
    • Organizer
      日本薬学会 第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 温度応答性分子による生体イメージングの基礎研究2018

    • Author(s)
      唐澤悟、青木伊知男、村山周平、臼井一晃
    • Organizer
      第95回日本生理学会大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高い水プロトン緩和能を有する超分子ガドリニウム錯体から成るMRI造影剤の構築2017

    • Author(s)
      荒木健、村山周平、臼井一晃、平井剛、青木伊知男、唐澤悟
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      東京
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 発光性1,5-ナフチリジン誘導体によるアミン応答性の検討2017

    • Author(s)
      廣田涼子、萩原隆介、臼井一晃、平井剛、唐澤悟
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      東京
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] [5]ヘリセン型ホスフィン配位子の合成とパラジウム触媒不斉反応への展開2017

    • Author(s)
      臼井一晃、山本耕介、清水貴士、井川和宣、友岡克彦、末宗洋、平井剛
    • Organizer
      第27回万有福岡シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] α-ケトアミドを基盤とする新しい光親和性標識実験用プローブの開発2017

    • Author(s)
      平井剛、太田英介、臼井一晃、大沼可奈、袖岡幹子
    • Organizer
      日本ケミカルバイオロジー学会 第12回年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 木谷憲昭、日高悠、臼井一晃、平井剛2017

    • Author(s)
      ラジカルカップリング反応を基盤とする炭素連結型2糖アナログの合成研究
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 三宅由希子、臼井一晃、太田英介、袖岡幹子、平井剛2017

    • Author(s)
      光親和性標識を目指した一置換α-ケトアミドの光反応性に関する理論的研究
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 有機ラジカル-ナノ微粒子の自己集合化挙動とMRI造影剤への応用2017

    • Author(s)
      森下晃佑、村山周平、臼井一晃、成田望実、平井剛、青木伊知男、唐澤悟
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] [5]ヘリセンの螺旋構造を基盤としたホスフィン配位子の合成と不斉触媒反応への応用2017

    • Author(s)
      臼井一晃、山本耕介、清水貴士、井川和宣、友岡克彦、平井剛、末宗洋
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 温度応答性超分子を用いたがん集積システムの開発2017

    • Author(s)
      唐澤 悟、荒木健、村山周平、臼井一晃、青木伊知男
    • Organizer
      第55回日本生物物理学会年会  シンポジウム「温度と生物の接点」
    • Related Report
      2017 Annual Research Report
  • [Presentation] Rational Design and Synthesis of [5]Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions2017

    • Author(s)
      臼井一晃
    • Organizer
      平成29年度 第二回有機合成化学講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Photoredox 触媒を用いたクロスカップリングによるアリール C- グリコシドの合成研究2017

    • Author(s)
      長門石昌孝、郭義天、臼井一晃、平井剛
    • Organizer
      第34回日本薬学会九州支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] クマリン縮環型ヘリセン誘導体の不斉合成とその固体・溶液状態における蛍光特性評価2016

    • Author(s)
      山本耕介、上野祐平、井川和宜、友岡克彦、平井剛、末宗洋
    • Organizer
      第10回 有機π電子系シンポジウム
    • Place of Presentation
      京都府京都市
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 螺旋構造内部空間を反応場とするヘリセン型配位子の開発2016

    • Author(s)
      臼井一晃
    • Organizer
      第10回 有機π電子系シンポジウム
    • Place of Presentation
      京都府京都市
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ヘリセン型ホスフィン配位子を用いた不斉アリル位置換反応と新規π拡張型ヘリセニルホスフィン配位子の合成2016

    • Author(s)
      横尾淳、清水貴士、井川和宣、友岡克彦、山本耕介、平井剛、末宗洋、臼井一晃
    • Organizer
      第33回 日本薬学会九州支部大会
    • Place of Presentation
      鹿児島県鹿児島市
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
  • [Presentation] 螺旋空間を利用した新規不斉リン配位子の開発と不斉触媒反応への応用2016

    • Author(s)
      臼井一晃
    • Organizer
      第33回 日本薬学会九州支部大会
    • Place of Presentation
      鹿児島県鹿児島市
    • Year and Date
      2016-12-03
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ヘリセン型ホスフィン配位子の開発とパラジウム触媒不斉反応への展開2016

    • Author(s)
      臼井一晃、山本耕介、清水貴士、井川和宣、友岡克彦、平井剛、末宗洋
    • Organizer
      第42回 反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡県静岡市
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] キラル[5]ヘリセニルホスフィンの合成とパラジウム触媒不斉アリル位置換反応への応用2016

    • Author(s)
      臼井一晃、長門石昌孝、清水貴士、井川和宣、友岡克彦、山本耕介、平井剛、末宗洋
    • Organizer
      第46回 複素環化学討論会
    • Place of Presentation
      石川県金沢市
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] ヘテロスピン鉄量子磁石の構造と光照射前後の磁性2016

    • Author(s)
      森昂也、臼井一晃、古賀登、唐澤悟
    • Organizer
      第10回 分子科学討論会
    • Place of Presentation
      兵庫県神戸市
    • Year and Date
      2016-09-13
    • Related Report
      2016 Research-status Report
  • [Presentation] Structures and magnetic properties of carbene-Fe(II) complexes having the intraMolecular ferromagnetic interaction2016

    • Author(s)
      Koya Mori, Kazuteru Usui, Noboru Koga, Satoru Karasawa
    • Organizer
      The 15th international conference on molecule-based magnets (ICMM2016)
    • Place of Presentation
      宮城県仙台市
    • Year and Date
      2016-09-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 長波長発光を示すヘキサアザペンタセン誘導体の合成2016

    • Author(s)
      廣田涼子、臼井一晃、古賀登、唐澤悟
    • Organizer
      第53回 化学関連支部合同九州大会
    • Place of Presentation
      福岡県北九州市
    • Related Report
      2016 Research-status Report
  • [Remarks] 優れた触媒性能を示す高機能らせん配位子の開発に成功

    • URL

      http://www.phar.kyushu-u.ac.jp/bbs/view1.php?S_Publ_Year=&word=&page=1&B_Code=348

    • Related Report
      2016 Research-status Report
  • [Remarks] 優れた触媒性能を示す高機能らせん分子の開発に成功!

    • URL

      http://www.kyushu-u.ac.jp/ja/researches/view/56

    • Related Report
      2016 Research-status Report
  • [Remarks] がん組織の高い温度に反応し、ナノ微粒子が特異的に集積する仕組みを開発 ~副作用のないがん治療へ期待~

    • URL

      http://www.kyushu-u.ac.jp/ja/researches/view/94

    • Related Report
      2016 Research-status Report
  • [Remarks] がん組織の高い温度に反応し、ナノ微粒子が特異的に集積する仕組みを開発 ~副作用のないがん治療へ期待~

    • URL

      http://www.jst.jp/pr/announce/20170308/index.html

    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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