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Applications and development of highly active nickel catalyst for hydrogenation reaction

Research Project

Project/Area Number 21590002
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKitasato University

Principal Investigator

MAKINO Kazuishi  北里大学, 薬学部, 教授 (20302573)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords触媒的不斉反応 / 不斉水素化 / 触媒 / フェロセン / ニッケル / 動的速度論分割 / 不斉水素化反応
Research Abstract

Asymmetric hydrogenation reactions of.-amino aromatic ketone using the nickel catalyst prepared from nickel acetate tetrahydrate, the chiral bidentate phosphine ligand, and NaBArF were examined. It was found that highly anti-and enantioselective selective asymmetric hydrogenation through dynamic kinetic resolution(DKR) proceeded in the presence of sodium acetate(1 equiv) as a base and in toluene under hydrogen pressure(100 atm).

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (64 results)

All 2012 2011 2010 2009 Other

All Journal Article (15 results) (of which Peer Reviewed: 8 results) Presentation (45 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Regioselective glycosylation of unprotected methyl hexopyranoside by transient masking with arylboronic acid2012

    • Author(s)
      Nishino, T.; Ohya, Y.; Murai, R.; Shirahata, T.; Yamamoto, D.; Makino, K.; Kaji, E
    • Journal Title

      Heterocycles

      Volume: 84 Issue: 2 Pages: 1123-1140

    • DOI

      10.3987/com-11-s(p)94

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Sequential one-pot glycosylation with glycosyl N-trichloroacety lcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars2011

    • Author(s)
      Shirahata, T.; Kojima, Teruya, S.; Matsuo, J.; Yokoyama, M.; Unagiike, S.; Sunazuka, T.; Makino, K.; Kaji, E.; Omura, S.; Kobayashi, Y
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 35 Pages: 6842-6896

    • DOI

      10.1016/j.tet.2011.06.006

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Diastereo-and enantioselective hydrogenation ofα-Amino-ss-keto ester hydrochlorides catalyzed by an iridium complex with MeO-BIPHEP and NaBArF : catalytic cycle and five-membered chelation mechanism of asymmetric hydroge nation2010

    • Author(s)
      Maeda, T.; Makino, K.; Iwasaki, M.; Hamada, Y
    • Journal Title

      Chem. Eur. J.

      Pages: 11954-1196

    • Related Report
      2011 Final Research Report
  • [Journal Article] Diastereo- and Enantioselective Hydrogenation of α-Amino-β-Keto Ester Hydrochlorides Catalyzed by an Iridium Complex with MeO-BIPHEP and NaBArF : Catalytic Cycle and Five-Membered Chelation Mechanism of Asymmetric Hydrogenation.2010

    • Author(s)
      Makino, K.
    • Journal Title

      Chem.Eur.J.

      Volume: 16 Pages: 11954-11962

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective aziridination reaction ofα, ss-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesul fonyloxycarbamates2009

    • Author(s)
      Arai, H.; Sugaya, N.; Sasaki, N.; Makino, K.; Lectard, S.; Hamada, Y
    • Journal Title

      Tetrahedron Lett

      Volume: 50 Pages: 183-186

    • Related Report
      2011 Final Research Report
  • [Journal Article] Reagent-controlled diastereoselective synthes is of(2S, 3R)-and(2R, 3R)-2, 3-diaminobutanoic acid derivatives using proline-catalyzedα-hydarazination reaction2009

    • Author(s)
      Makino, K.; Kubota, S.; Hara, S.; Sakaguchi, M.; Hamajima, A.; Hamada, Y.
    • Journal Title

      Tetrahedron

      Volume: 65 Pages: 9468-9473

    • Related Report
      2011 Final Research Report
  • [Journal Article] Total synthesis of halipeptin D2009

    • Author(s)
      Sakaguchi, M.; Hara, S.; Koma, Y.; Makino, K.; Hamada, Y.
    • Journal Title

      Peptide Science

      Pages: 183-186

    • NAID

      10027166173

    • Related Report
      2011 Final Research Report
  • [Journal Article] Highly stereoselective synthesis of(2R, 3R)-2-amino-3-cyclohexyl-3-hydroxypropionic acid using asymmetric hydrogenation2009

    • Author(s)
      Makino, K.; Goto, T.; Ohtaka, J.; Hamada, Y.
    • Journal Title

      Heterocycles

      Volume: 77 Pages: 629-634

    • NAID

      40016405904

    • Related Report
      2011 Final Research Report
  • [Journal Article] Homogeneous chiral nickel-catalyzed asymmetric hydrogenation of substituted aromaticα-aminoketone hydrochlorides through dynamic kinetic resolution2009

    • Author(s)
      Hibino, T.; Makino, K.; Sugiyama, T.; Hamada, Y.
    • Journal Title

      Chem Cat Chem

      Volume: 1 Pages: 237-240

    • Related Report
      2011 Final Research Report
  • [Journal Article] Reagent-controlled diastereoselective synthesis of(2S,3R)-and(2S,3R)-2,3-diaminobutanoic acid derivatives using proline-catalyzed α-hydarazination reaction.2009

    • Author(s)
      Kazuishi Makino
    • Journal Title

      Tetrahedron, 65

      Pages: 9468-9473

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly stereoselective synthesis of(2R,3R)-2-amino-3-cyclohexyl-3-hydroxypropionic acid using asymmetric hydrogenation.2009

    • Author(s)
      Kazuishi Makino
    • Journal Title

      Heterocycles 77

      Pages: 629-634

    • NAID

      40016405904

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Homogeneous Chiral Nickel-Catalyzed Asymmetric Hydrogenation of Substituted Aromatic α-Aminoketone Hydrochlorides through Dynamic Kinetic Resolution.2009

    • Author(s)
      Kazuishi Makino
    • Journal Title

      ChemCatChem, 1

      Pages: 237-240

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates.2009

    • Author(s)
      Kazuishi Makino
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 3329-3332

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of halipeptin D2009

    • Author(s)
      Kazuishi Makino
    • Journal Title

      Peptide Science

      Pages: 183-186

    • NAID

      10027166173

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article]2009

    • Author(s)
      Yasumasa Hamada, Kazuishi Makino
    • Journal Title

      Asymmetric Synthesis and Application of α-Amino Acids(米国化学会)

      Pages: 227-238

    • Related Report
      2009 Annual Research Report
  • [Presentation] アルドース還元酵素阻害作用をもつPaeoniflorin類の合成研究2012

    • Author(s)
      淺川俊也
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] 有機ホウ素化合物の分子認識能を利用したアミノ糖の位置選択的グリコシル化反応の開発2012

    • Author(s)
      増田貴帆
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] 糖4位に桂皮酸を有するサポニンの合成研究-22012

    • Author(s)
      勝見達也
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] SO_3H修飾シリカゲルを用いた脱保護反応の検討2012

    • Author(s)
      長瀬博
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 機能性糖鎖探索のための糖鎖ライブラリーの構築2012

    • Author(s)
      牧野一石
    • Organizer
      第29回白金シンポジウム・北里大学薬学部「文部科学省ハイテク・リサーチ・センター整備事業」研究成果最終報告会
    • Place of Presentation
      東京
    • Year and Date
      2012-01-18
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] キラルスルホキシドの合成と不斉アリル化反応への応用2011

    • Author(s)
      牧野一石
    • Organizer
      AKPS集会第7回北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-12-22
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 抗ウイルス性抗生物質ファッティビラシン-8の全合成研究2011

    • Author(s)
      牧野一石
    • Organizer
      AKPS集会第7回北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-12-22
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] グリコシルカルバメートとトリクロロアセテートを用いた簡便な糖鎖連結の方法論の開発2011

    • Author(s)
      小林義典
    • Organizer
      AKPS集会第7回北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-12-22
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 糖4位に桂皮酸エステルを有するサポニンの合成研究2011

    • Author(s)
      小林義典
    • Organizer
      AKPS集会第7回北里化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2011-12-22
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] Synthetic Studies on(-)-Paeonihybridin, a Monoterpene Glycosides with Aldose Reductase Inhibitory Activity2011

    • Author(s)
      Makino, K.
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium(AIMECS)
    • Place of Presentation
      Tokyo
    • Year and Date
      2011-11-30
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthetic Studies on (-)-Paeonihybridin, a Monoterpene Glycosides with Aldose Reductase Inhibitory Activity2011

    • Author(s)
      山本大介
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium (AIMECS)
    • Place of Presentation
      東京
    • Year and Date
      2011-11-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] One-pot, regioselective glycosylation of free sugars by means of masking through bisboronate intermediates2011

    • Author(s)
      Kaji, E.
    • Organizer
      16th European Carbohydrate Symposium
    • Place of Presentation
      Naples, Italy
    • Year and Date
      2011-07-03
    • Related Report
      2011 Final Research Report
  • [Presentation] One-pot, Regioselective Glycosylation of Free Sugars by Means of Masking Through Bisboronate Intermediates2011

    • Author(s)
      梶英輔
    • Organizer
      16th European Carbohydrate Symposium
    • Place of Presentation
      Naples, Italy
    • Year and Date
      2011-07-03
    • Related Report
      2011 Annual Research Report
  • [Presentation] 抗ウイルス性抗生物質ファッティビラシン関連化合物の合成研究2011

    • Author(s)
      牧野一石
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] 糖尿病治療薬開発を指向したペオニヒブリジンの合成研究2011

    • Author(s)
      牧野一石
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] β(1→3, 6)分枝ガラクトオリゴ糖の簡易合成およびクラスター化2011

    • Author(s)
      牧野一石
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] アリールボロン酸存在下での無保護糖供与体によるグリコシル化反応2011

    • Author(s)
      牧野一石
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] 基礎系教員と薬学生による共同リサーチ:医療連携2011

    • Author(s)
      鈴木順子
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] 基礎系教員と薬学生による共同リサーチ:医療連携2011

    • Author(s)
      牧野一石
    • 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
  • [Presentation] 糖4位に桂皮酸エステルを有するサポニンの合成研究その22011

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-29
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] グリコシルカルバメートとトリクロロアセテートを用いた簡便な糖鎖連結の方法論の開発2010

    • Author(s)
      小林義典
    • Organizer
      第60回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2010-12-04
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Presentation] Regioselective glycosylation of fully unprotected sugars by means of molecular recognition using aryboronic acids2010

    • Author(s)
      Kaji, E.
    • Organizer
      25th International carbohydrate symposium
    • Place of Presentation
      Chiba
    • Year and Date
      2010-08-03
    • Related Report
      2011 Final Research Report
  • [Presentation] Regioselective glycosylation of fully unprotected sugars by means of molecular recognition using aryboronic acids2010

    • Author(s)
      Makino K.
    • Organizer
      25^<th> International carbohydrate symposium
    • Place of Presentation
      千葉
    • Year and Date
      2010-08-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] アルドース還元酵素阻害作用をもつPaeoniflorin類の合成研究2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2010-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] 有機ホウ素化合物の分子認識能を利用したアミノ糖の位置選択的グリコシル化反応の開発2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2010-03-30
    • Related Report
      2011 Final Research Report
  • [Presentation] 糖4位に桂皮酸を有するサポニンの合成研究-22010

    • Author(s)
      小林義典
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2010-03-30
    • Related Report
      2011 Final Research Report
  • [Presentation] 抗ウイルス性抗生物質ファッティビラシン関連化合物の全合成研究2010

    • Author(s)
      梶英輔
    • Organizer
      日本薬学会130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] グルコシルカルバメートとカルバチオエートを用いた簡便な糖鎖連結の方法論の開発2010

    • Author(s)
      梶英輔
    • Organizer
      日本薬学会130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] シクロフラクタン系新規包接素材の開発を指向したフルクトオリゴ糖の合成研究2010

    • Author(s)
      梶英輔
    • Organizer
      日本薬学会130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] アリールボロン酸の分子認識を利用した遊離糖の位置選択的グリコシル化反応の開発2010

    • Author(s)
      梶英輔
    • Organizer
      日本薬学会130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] 海洋産環状デプシペプチドパプアミドBの全合成研究2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] 抗ウイルス性抗生物質ファッティビラシン関連化合物の全合成研究2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] グルコシルカルバメートとカルバチオエートを用いた簡便な糖鎖連結の方法論の開発2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] シクロフラクタン系新規包接素材の開発を指向したフルクトオリゴ糖の合成研究2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] アリールボロン酸の分子認識を利用した遊離糖の位置選択的グリコシル化反応の開発2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] プロリン誘導体を用いた不斉アジリジン化反応の開発2010

    • Author(s)
      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
      2011 Final Research Report
  • [Presentation] 海洋産環状デプシペプチドPapuamideAの全合成研究2010

    • Author(s)
      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
      2011 Final Research Report
  • [Presentation] 海洋産環状デプシペプチドパプアミドBの全合成研究2010

    • Author(s)
      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
      2011 Final Research Report
  • [Presentation] プロリン誘導体を用いた不斉アジリジン化反応の開発2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 海洋産環状デプシペプチドPapuamideAの全合成研究2010

    • Author(s)
      牧野一石
    • Organizer
      日本薬学会130年会(岡山)
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] アリールボロン酸の分子認識を利用した遊離糖の位置選択的グリコシル化反応の開発2009

    • Author(s)
      梶英輔
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟・長岡
    • Year and Date
      2009-11-29
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] シクロフラクタン系新規包接素材の開発を指向したフルクトオリゴ糖の合成研究2009

    • Author(s)
      梶英輔
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟・長岡
    • Year and Date
      2009-11-29
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] 有機触媒を用いたMartinellineの不斉全合成2009

    • Author(s)
      濱田康正
    • Organizer
      第7回次世代シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2009-07-24
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Presentation] ニッケル錯体を用いたα-アミノケトン類の触媒的不斉水素化反応の開発2009

    • Author(s)
      濱田康正
    • Organizer
      第57回有機合成化学協会関東支部シンポシウム
    • Place of Presentation
      東京
    • Year and Date
      2009-05-09
    • Related Report
      2011 Final Research Report
  • [Presentation] ニックル錯体を用いたα-アミノケトン類の触媒的不斉水素化反応の開発2009

    • Author(s)
      牧野一石
    • Organizer
      第57回有機合成化学協会関東支部シンポシウム
    • Place of Presentation
      東京
    • Year and Date
      2009-05-09
    • Related Report
      2009 Annual Research Report
  • [Book] 基礎有機化学2012

    • Author(s)
      牧野一石
    • Publisher
      培風館
    • Related Report
      2011 Final Research Report
  • [Book] 無機化合物・錯体-生物無機化学の基礎2010

    • Author(s)
      牧野一石
    • Publisher
      廣川書店
    • Related Report
      2011 Final Research Report 2010 Annual Research Report
  • [Book] Asymmetric Synthesis and Application ofα-Amino Acids2009

    • Author(s)
      Hamada, Y.; Makino, K.
    • Publisher
      American Chemical Society
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.pharm.kitasato-u.ac.jp/medicinal/Welcome.html

    • Related Report
      2011 Final Research Report

URL: 

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

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