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Asymmetric Cyanation and Hydrogenation Catalyzed by Ruthenium Complexes

Research Project

Project/Area Number 24350042
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

OHKUMA Takeshi  北海道大学, 工学(系)研究科(研究院), 教授 (50201968)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥18,330,000 (Direct Cost: ¥14,100,000、Indirect Cost: ¥4,230,000)
Fiscal Year 2014: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2013: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2012: ¥7,020,000 (Direct Cost: ¥5,400,000、Indirect Cost: ¥1,620,000)
Keywords触媒的不斉合成 / 不斉シアノ化反応 / 不斉水素化反応 / ケトン / イミン / シアン化化合物 / アルコール / アミン
Outline of Final Research Achievements

Chiral Ru-Li combined systems developed by our research group efficiently catalyzed 1) hydrocyanation of aldehydes and N-protected aldimines, 2) cyanosilylation of simple and α-alkoxy ketones, and 3) conjugate hydrocyanation of α,β-unsaturated ketones and N-acylpyrroles. The substrate-to-catalyst molar ratio of 10,000 and enantioselectivity of 99% were achieved in the best cases.
The novel chiral Ru complexes achieved 1) very rapid and highly enantioselective hydrogenation of ketones, 2) asymmetric hydrogenation of N-arylimines, quinoxalines, and benzoxazines. The rate (turnover frequency) of the hydrogenation of ketones reached about 35,000 per minute with grater than 99% enantioselectivity. The turnover number of 18,000 and enantioselectivity of 99% in the reaction of N-arylimines were obtained in the best cases.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (76 results)

All 2015 2014 2013 2012 Other

All Journal Article (14 results) (of which Peer Reviewed: 13 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (45 results) (of which Invited: 5 results) Book (1 results) Remarks (6 results) Patent(Industrial Property Rights) (10 results) (of which Overseas: 2 results)

  • [Journal Article] Novel Intramolecular Cyclization-Skeletal Reorganization of 2-Arylthiazoles under Photoirradiation2015

    • Author(s)
      Noriyoshi Arai, Moe Mizota, Takeshi Ohkuma
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 1 Pages: 607-616

    • DOI

      10.3987/com-14-s(k)8

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Stereoselective Preparation of Spiro[4.4] Cyclic Compounds by the Photochemical Activation of Oxazoles2015

    • Author(s)
      Noriyoshi Arai, Moe Mizota, Takeshi Ohkuma
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 1 Pages: 86-89

    • DOI

      10.1021/ol5032848

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] ケトン類およびイミン類の環境調和型不斉水素化触媒の開発と応用2015

    • Author(s)
      大熊 毅
    • Journal Title

      ファルマシア

      Volume: 51 Pages: 295-299

    • NAID

      130007448048

    • Related Report
      2014 Annual Research Report
  • [Journal Article] Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles with the Ru(phgly)2(binap)-CH3OLi Catalyst System2014

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Kohei Yamauchi, Takeshi Ohkuma
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 3 Pages: 808-811

    • DOI

      10.1021/ol403545b

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 8-Oxoberbines and Related Benzolactams by Pd(OAc)2-Catalyzed Direct Aromatic Carbonylation2013

    • Author(s)
      Mamoru Miyazawa, Takashi Tokuhashi, Akiyoshi Horibata, Takatoshi Nakamura, Yu Onozaki, Nobuhito Kurono, Hisanori Senboku, Masato Tokuda, Takeshi Ohkuma, Kazuhiko Orito
    • Journal Title

      J. Heterocyclic Chem.

      Volume: 50 Issue: S1

    • DOI

      10.1002/jhet.1044

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of Diastereomerically Pure and Mixed (S)-PhGly/BIPHEP/Ru(II) Complexes and Their Catalytic Behavior with Li2CO3 in Asymmetric Cyanosilylation of Benzaldehyde2013

    • Author(s)
      Nobuhito Kurono, Taiki Katayama, Takeshi Ohkuma
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 86 Issue: 5 Pages: 577-582

    • DOI

      10.1246/bcsj.20120351

    • NAID

      10031167849

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Alkynyl Ketones with the η6-Arene/TsDPEN-Ruthenium(II) Catalyst2013

    • Author(s)
      Noriyoshi Arai, Hironori Satoh, Noriyuki Utsumi, Kunihiko Murata, Kunihiko Tsutsumi, Takeshi Ohkuma
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 12 Pages: 3030-3033

    • DOI

      10.1021/ol4012184

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehydes with the tol-binap/dbapen/Ruthenium(II) Catalyst2013

    • Author(s)
      Noriyoshi Arai, Keisuke Sato, Keita Azuma, Takeshi Ohkuma
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 29 Pages: 7500-7504

    • DOI

      10.1002/anie.201303423

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Quinoxalines, Benzoxazines, and a Benzothiazine Catalyzed by Chiral Ruthenabicyclic Complexes2013

    • Author(s)
      Noriyoshi Arai, Yu Saruwatari, Kotaro Isobe, Takeshi Ohkuma
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Issue: 14-15 Pages: 2769-2774

    • DOI

      10.1002/adsc.201300604

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design of Molecular Catalysts for Achievement of High Turnover Number in Homogeneous Hydrogenation2012

    • Author(s)
      N. Arai
    • Journal Title

      Chem. Rec.

      Volume: VOL.12 Issue: 2 Pages: 284-289

    • DOI

      10.1002/tcr.201100019

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Cyanosilylation of Ketones with Amino Acid/BINAP/Ruthenium(II)-Lithium Phenoxide Catalyst Systems2012

    • Author(s)
      M. Uemura
    • Journal Title

      Adv. Synth. Catal.

      Volume: VOL.354 Issue: 10 Pages: 2023-2030

    • DOI

      10.1002/adsc.201200027

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cyanation with the Chiral Ru-Li Combined Catalysts'2012

    • Author(s)
      T. Ohkuma
    • Journal Title

      Synlett

      Volume: VOL.23 Issue: 13 Pages: 1865-1881

    • DOI

      10.1055/s-0032-1316545

    • NAID

      120005306774

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a 3-Arylisoquinoline Alkaloid, Decumbenine B2012

    • Author(s)
      E. Kumazawa
    • Journal Title

      Eur. J. Ore. Chem.

      Volume: 2012 Issue: 24 Pages: 4622-4633

    • DOI

      10.1002/ejoc.201200262

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of N-Arylimines Catalyzed by the Xyl-Skewphos/DPEN-Ruthenium(II)2012

    • Author(s)
      N. Arai
    • Journal Title

      Adv. Synth, Catal.

      Volume: VOL.354 Issue: 11-12 Pages: 2089-2095

    • DOI

      10.1002/adsc.201200464

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] アルキン誘導体安定化パラジウムナノ粒子触媒を用いる高選択的水素化反応2015

    • Author(s)
      小野寺希望、新井則義、出耒田 敦、堀 順一、大熊 毅
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス/薬学部(船橋)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルRu/Li複合触媒によるα-イミノエステル類の不斉シアノ化反応2015

    • Author(s)
      鈴木一聡、坂口祐介、新田梨乃、黒野暢仁、大熊 毅
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス/薬学部(船橋)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルRu/Li複合触媒によるアルキニルケトン類の不斉シアノシリル化反応2015

    • Author(s)
      山内康平、坂口祐介、黒野暢仁、大熊 毅
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス/薬学部(船橋)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carboxylic Acid Derivatives Catalyzed by the Ruthenium Complex/Lithium Compound Combined Systems2015

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Takeshi Ohkuma
    • Organizer
      北海道大学大学院総合化学院創設5周年記念研究発表会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2015-03-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Selective Hydrogenation Catalyzed by Alkyne Derivatives-Stabilized Palladium Nanoparticles2015

    • Author(s)
      Nozomi Onodera, Noriyoshi Arai, Takeshi Ohkuma
    • Organizer
      北海道大学大学院総合化学院創設5周年記念研究発表会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2015-03-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation and Isomerization Catalyzed by Ruthenium(II) Complexes2014

    • Author(s)
      Takeshi Ohkuma
    • Organizer
      8th Singapore International Chemistry Conference 2014
    • Place of Presentation
      National University of Singapore (University Town, Singapore)
    • Year and Date
      2014-12-16
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Enantioselective Hydrogenation and Isomerization with Chiral Ruthenium(II) Catalysts2014

    • Author(s)
      Takeshi Ohkuma
    • Organizer
      The 9th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Eastin Hotel (Petaling Jaya, Malaysia)
    • Year and Date
      2014-12-02
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ルテニウム錯体触媒を用いる不斉水素化反応の開発2014

    • Author(s)
      大熊 毅
    • Organizer
      日産化学学術講演会
    • Place of Presentation
      日産化学物質化学研究所(船橋)
    • Year and Date
      2014-11-19
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 分子サイズのロボット=分子触媒による不斉水素化反応2014

    • Author(s)
      大熊 毅
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-10-15
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Hydrogenation of Nitrogen Heteroaromatics Catalyzed by Chiral Ruthenabucyclic Complexes2014

    • Author(s)
      Noriyoshi Arai, Yu Saruwatari, Kotaro Isobe, Takeshi Ohkuma
    • Organizer
      The 24th French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      University Claude Bernard Lyon 1(Lyon, France)
    • Year and Date
      2014-09-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] 医薬中間体「光学活性アルコール」の実用的製法2014

    • Author(s)
      大熊 毅
    • Organizer
      イノベーションジャパン2014
    • Place of Presentation
      東京ビックサイト(東京都江東区)
    • Year and Date
      2014-09-11 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 光学活性1-(2,6-Dichloro-3-fluorophenyl)ethanolの実用的製法の開発2014

    • Author(s)
      片山武昭、新井則義、難波孝則、村田邦彦、堤 邦彦、大熊 毅
    • Organizer
      日本プロセス化学会 2014サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-08-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] Enantioselective 1,3-Hydrogen Migration of Primary Allylic Alcohols Catalyzed by Diphosphine-Ru(II) Complexes2014

    • Author(s)
      Noriyoshi Arai, Keisuke Sato, Takeshi Ohkuma
    • Organizer
      The XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(札幌)
    • Year and Date
      2014-07-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Alkynyl Ketones with the η6-Arene/TsDPEN-Ruthenium(II) Catalyst2014

    • Author(s)
      Hironori Satoh, Noriyoshi Arai, Takeshi Ohkuma
    • Organizer
      The XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(札幌)
    • Year and Date
      2014-07-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carboxylic Acid Derivatives Catalyzed by the Ruthenium Complex/Lithium Compound Combined Systems2014

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Takeshi Ohkuma
    • Organizer
      The XXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(札幌)
    • Year and Date
      2014-07-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] オキサゾール類およびチアゾール類の光活性化を利用した新規分子内環化反応2014

    • Author(s)
      溝田 萌、新井則義、大熊 毅
    • Organizer
      日本化学会北海道支部2014年夏季研究発表会
    • Place of Presentation
      苫小牧工業高等専門学校(苫小牧)
    • Year and Date
      2014-07-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルキン誘導体安定化パラジウムナノ粒子触媒を用いる高選択的水素化反応2014

    • Author(s)
      小野寺希望、新井則義、大熊 毅
    • Organizer
      日本化学会北海道支部2014年夏季研究発表会
    • Place of Presentation
      苫小牧工業高等専門学校(苫小牧)
    • Year and Date
      2014-07-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルキン誘導体安定化パラジウムナノ粒子を用いるアルキン類の部分水素化反応2014

    • Author(s)
      小野寺希望、新井則義、大熊 毅
    • Organizer
      第26回万有札幌シンポジウム
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carboxylic Acid Derivatives Catalyzed by the Ruthenium Complex/Lithium Compound Combined Systems2014

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Takeshi Ohkuma
    • Organizer
      The 3rd Frontier Chemistry Center International Symposium
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-06-13 – 2014-06-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] η^6-Arene/TsDPEN-Ru(II)錯体触媒を用いるアルキニルケトン類の不斉水素化反応2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-24
    • Related Report
      2012 Annual Research Report
  • [Presentation] 新規ルテナビシクロ錯体触媒を用いたキノキサリン類の不斉水素化反応2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-24
    • Related Report
      2012 Annual Research Report
  • [Presentation] アルキン誘導体を保護剤としたPdナノ粒子によるニトロアレーン類の高効率かつ官能基選択的水素2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-23
    • Related Report
      2012 Annual Research Report
  • [Presentation] BINAP/DBAPEN-Ru(II)錯体触媒を用いたアリルアルコール類の不斉異性化反応2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-23
    • Related Report
      2012 Annual Research Report
  • [Presentation] キラル銅錯体を用いたα,α-二置換α-ヒドロキシエステル類のエナンチオマー選択的カルバモイル2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Annual Research Report
  • [Presentation] ルテニウムリチウム複合錯体触媒を用いる α,β-不飽和カルボニル化合物の不斉共役シアノ化反応2013

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス、草津(滋賀)
    • Year and Date
      2013-03-22
    • Related Report
      2012 Annual Research Report
  • [Presentation] キラル銅触媒によるα-ヒドロキシエステル類の速度論分割2013

    • Author(s)
      大熊 毅
    • Organizer
      JST推薦シーズ 新技術説明会
    • Place of Presentation
      JST東京本部別館ホール、市ヶ谷(招待講演)
    • Year and Date
      2013-03-11
    • Related Report
      2012 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation for Practical Synthesis of Chiral Molecules2013

    • Author(s)
      大熊 毅
    • Organizer
      The 4th Symposium on Academic Exchange and Collaborative Research between MRC-ETHZ and FoE-HU
    • Place of Presentation
      北海道大学、札幌(招待講演)
    • Year and Date
      2013-02-21
    • Related Report
      2012 Annual Research Report
  • [Presentation] 医薬原料「光学活性アルコール類」の工業的合成 -NEDO成功事例紹介-2013

    • Author(s)
      大熊 毅
    • Organizer
      イノベーションジャパン2013
    • Place of Presentation
      東京ビックサイト、東京都江東区
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carbonyl Compounds Catalyzed by the Ruthenium Complex/Lithium Compound Combined Systems2013

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Takeshi Ohkuma
    • Organizer
      10th International Symposium on Carbanion Chemistry
    • Place of Presentation
      京都国際会議場、京都
    • Related Report
      2013 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carbonyl Compounds Catalyzed by the Ruthenium Complex/Lithium Compound Combined Systems2013

    • Author(s)
      Yusuke Sakaguchi, Nobuhito Kurono, Takeshi Ohkuma
    • Organizer
      Frontier Chemistry Center The 2nd International Symposium
    • Place of Presentation
      北海道大学、札幌
    • Related Report
      2013 Annual Research Report
  • [Presentation] Construction of Fused Ring Frameworks through a Novel Photocyclization of α-Arylthiophene Derivatives2012

    • Author(s)
      大熊 毅
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Year and Date
      2012-11-15
    • Related Report
      2012 Annual Research Report
  • [Presentation] RUCY (Chiral Ruthenabicyclic Complexes) : Pre-catalyst for Rapid, Enantioselective, and Wide-scope Hydrogenation of Ketones2012

    • Author(s)
      大熊 毅
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Year and Date
      2012-11-14
    • Related Report
      2012 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Imines Catalyzed by the Xylskewphos/DPEN-Ruthenium(II)Complex2012

    • Author(s)
      大熊 毅
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Year and Date
      2012-11-14
    • Related Report
      2012 Annual Research Report
  • [Presentation] Catalyst-Controlled Diastereoselection in the Asymmetric Hydrogenation of Heterocycloalkyl Ketones2012

    • Author(s)
      大熊 毅
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Year and Date
      2012-11-14
    • Related Report
      2012 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Ketones Catalyzed by the Ruthenium2012

    • Author(s)
      大熊 毅
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Year and Date
      2012-11-13
    • Related Report
      2012 Annual Research Report
  • [Presentation] Construction of Fused Ring Framework by Photochemical Activation of Furan and Thiophene Derivatives2012

    • Author(s)
      大熊 毅
    • Organizer
      Polish-Japanese Seminar
    • Place of Presentation
      AGH University of Science and Technology, Cracow (Poland)
    • Year and Date
      2012-09-05
    • Related Report
      2012 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Carbonyl Compounds2012

    • Author(s)
      大熊 毅
    • Organizer
      Polish-Japanese Seminar
    • Place of Presentation
      AGH University of Science and Technology, Cracow (Poland)
    • Year and Date
      2012-09-05
    • Related Report
      2012 Annual Research Report
  • [Presentation] ルテナビシクロ錯体触媒を用いるキノキサリン類の不斉水素化反応2012

    • Author(s)
      大熊 毅
    • Organizer
      日本化学会北海道支部2012年夏季研究発表会
    • Place of Presentation
      旭川工業高等専門学校、旭川
    • Year and Date
      2012-08-04
    • Related Report
      2012 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Ketones and Imines Catalyzed by Ru(II)Complexes2012

    • Author(s)
      大熊 毅
    • Organizer
      2012 Hokkaido University & Peking University Joint Symposium
    • Place of Presentation
      北海道大学、札幌(招待講演)
    • Year and Date
      2012-07-17
    • Related Report
      2012 Annual Research Report
  • [Presentation] ルテナビシクロ錯体触媒を用いたキノキサリン類の不斉水素化反応2012

    • Author(s)
      大熊 毅
    • Organizer
      第24回 万有札幌シンポジウム
    • Place of Presentation
      北海道大学、札幌
    • Year and Date
      2012-07-07
    • Related Report
      2012 Annual Research Report
  • [Presentation] η6-Arene/TsDPEN-Ru(II)錯体触媒を用いるアルキニルケトン類の不斉水素化反応

    • Author(s)
      佐藤裕典、新井則義、大熊 毅
    • Organizer
      第25回万有札幌シンポジウム
    • Place of Presentation
      北海道大学、札幌
    • Related Report
      2013 Annual Research Report
  • [Presentation] ルテニウム/リチウム複合錯体触媒を用いるα,β-不飽和カルボニル化合物の不斉共役シアノ化反応

    • Author(s)
      坂口祐亮、黒野暢仁、大熊 毅
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学、北見
    • Related Report
      2013 Annual Research Report
  • [Presentation] チオフェン類の光活性化を利用した新規炭素縮環系骨格構築手法の開発

    • Author(s)
      溝田 萌、田中皓一朗、新井則義、大熊 毅
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学、北見
    • Related Report
      2013 Annual Research Report
  • [Presentation] 光照射による2-アリールチアゾール類の新規分子内環化―骨格組み替え反応

    • Author(s)
      新井則義、溝田 萌、大熊 毅
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学・東山キャンパス、名古屋
    • Related Report
      2013 Annual Research Report
  • [Presentation] オキサゾール類の光活性化を利用した高立体選択的環化反応

    • Author(s)
      溝田 萌、新井則義、大熊 毅
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学・東山キャンパス、名古屋
    • Related Report
      2013 Annual Research Report
  • [Book] Comprehensive Chirality, Vol.5 (Reduction-Hydrogenation : C=○ ; Chemoselective )2012

    • Author(s)
      T. Ohkuma
    • Total Pages
      31
    • Publisher
      Elsevier
    • Related Report
      2012 Annual Research Report
  • [Remarks] 所属機関研究者ホームページ

    • URL

      http://researchers.general.hokudai.ac.jp/profile/ja.NdPJqMJLAsv96qNLmm41Sg==.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 研究室ホームページ

    • URL

      http://os-cp.eng.hokudai.ac.jp/os/Welcome.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 所属機関研究者ホームページ

    • URL

      http://researchers.general.hokudai.ac.jp/profile/ja.NdPJqMJLAsv96qNLmm41Sg==.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 研究室ホームページ

    • URL

      http://os-cp.eng.hokudai.ac.jp/os/Welcome.html

    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://researchers.general.hokudai.ac.jp/profile/ja.NdPJqMJLAsv96qNLmm41Sg==.html

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://os-cp.eng.hokudai.ac.jp/os/Welcome.html

    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性2級アルコールの製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学、関東化学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-156016
    • Filing Date
      2013-07-26
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性2級アルコールの製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学、関東化学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-156036
    • Filing Date
      2013-07-26
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性3-置換クロマン-4-オール化合物の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学、日本曹達
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2013-177329
    • Filing Date
      2013-08-28
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミン化合物の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2013-017845
    • Filing Date
      2013-01-31
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミン化合物の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Filing Date
      2013-01-31
    • Related Report
      2012 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 光学活性アミン化合物の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Filing Date
      2013-02-01
    • Related Report
      2012 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 光学活性アルデヒドの製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2013-044065
    • Filing Date
      2013-03-06
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性第三級アルコール誘導体の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2013-045569
    • Filing Date
      2013-03-07
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 芳香族アミン化合物の製造方法2013

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2013-045958
    • Filing Date
      2013-03-07
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミンの製造方法2012

    • Inventor(s)
      大熊 毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2012-197246
    • Filing Date
      2012-09-07
    • Related Report
      2012 Annual Research Report

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Published: 2012-04-24   Modified: 2019-07-29  

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