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Asymmetric Reactions Catalyzed by Metal Complexes with two Chiral Ligands

Research Project

Project/Area Number 21350048
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

OHKUMA Takeshi  北海道大学, 大学院・工学研究院, 教授 (50201968)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000)
Fiscal Year 2011: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2010: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2009: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Keywords触媒的不斉合成 / 不斉シアノシリル化反応 / 不斉水素化反応 / 金属錯体触媒 / アルデヒド / シアノヒドリン / ケトン / アルコール / 不斉ヒドリド転位反応
Research Abstract

Chiral Ru(II) and Ir(III) complexes developped by our research groupi efficiently catalyzed 1) asymmetric cyanosilylation of aldehydes and ketones, 2) asymmetric hydrogenation of ketones, and 3) asymmetric 1,3-hydride migration of allylic alcohols : 1) Enantioselectivity as high as 99% in the reaction with a substrate-to-catalyst molar ratio (S/C) of 10,000 was achieved. 2) A series of chiral alcohols which is hardly prepared by the other methods was readily synthesized in high enantioselectivity. One of these ractions has been commercialized in the synthetic process of a chiral medicine. 3) The highest enantioselectivity of 98% in the reaction with an S/C of 1000 was achieved

Report

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

    (82 results)

All 2012 2011 2010 2009 Other

All Journal Article (19 results) (of which Peer Reviewed: 18 results) Presentation (43 results) Book (3 results) Remarks (9 results) Patent(Industrial Property Rights) (8 results)

  • [Journal Article] Phosphate-Free Pd^o-Catalyzed Cycloamination and Carbonylation with Pd(OAc)_2 and Cu(OAc)_2 in the Presence of K_2CO_3 : Preparation of Benzocyclic Amines and Benzolactams2012

    • Author(s)
      R.Harada
    • Journal Title

      Eur.J.Org.Chem.

      Volume: 2012 Issue: 2 Pages: 366-379

    • DOI

      10.1002/ejoc.201101214

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Hydrocyanation of N-Protected Aldimines2012

    • Author(s)
      M.Uemura
    • Journal Title

      Org.Lett.

      Volume: VOL.14 Issue: 3 Pages: 882-885

    • DOI

      10.1021/ol203408w

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel Intramolecular Photocyclization of α-Arylthiophene Derivatives2012

    • Author(s)
      N.Arai
    • Journal Title

      Org.Lett.

      Volume: VOL.14 Issue: 6 Pages: 1488-1491

    • DOI

      10.1021/ol3002305

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalyst-Controlled Diastereoselection in the Hydrogenation of Heterocycloalkyl Ketones2011

    • Author(s)
      Masaya Akashi, Noriyoshi Arai, Tsutomu Inoue, Takeshi Ohkuma
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: Vol.353 Issue: 11-12 Pages: 1955-1960

    • DOI

      10.1002/adsc.201100398

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article]2011

    • Author(s)
      Kazuhiko Matsumura, Noriyoshi Arai, Kiyoto Hori, Takao Saito, Noboru Sayo, Takeshi Ohkuma
    • Journal Title

      Journal of the American Chemical Society

      Volume: Vol.133 Issue: 28 Pages: 10696-10699

    • DOI

      10.1021/ja202296w

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrocyanation of α,β-Unsaturated Ketones into β-Cyano Ketones with the [Ru(phgly)_2(binap)]/C_6H_5OLi Catalyst System2011

    • Author(s)
      黒野暢仁
    • Journal Title

      Angewwandte Chemie, International Editoin

      Volume: Vol.50 Issue: 24 Pages: 5541-5544

    • DOI

      10.1002/anie.201100939

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of Racemic α-tert-Alkyl-α-hydroxy Esters by Enantiomer-Selective Carbamoylation2011

    • Author(s)
      N.Kurono
    • Journal Title

      J.Org.Chem.

      Volume: VOL.76 Issue: 24 Pages: 10312-10318

    • DOI

      10.1021/jo201940w

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Hydrocyanation of Aldehydes Catalyzed by [Li {Ru(phgly) 2 (binap)}] X (X=Cl, Br).2011

    • Author(s)
      N.Kurono
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 1254-1257

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article]2010

    • Author(s)
      Noriyoshi Arai, Masaya Akashi, Satoshi Sugizaki, Hirohito Ooka Tsutomu Inoue, Takeshi Ohkuma
    • Journal Title

      Organic Letters

      Volume: Vol.12 Pages: 3380-3383

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral η^6-Arene/N-Tosylethylenediamine-Ruthenium(II) Complexes : Slution Behavior and Catalytic Activity for Asymmetric Hydrogenation.2010

    • Author(s)
      C.A.Sandoval
    • Journal Title

      Chem.Asian J.

      Volume: 5 Pages: 806-816

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/LPHAN-Ru(II) Complex.2010

    • Author(s)
      N.Arai
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 3380-3383

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Ininium Ene Reaction with Cu(I) Catalysts : Facile Formation of 4-Amino-3-methylenechromans from O-Propargyl Salicylaldehydes and Dialkylamines.2010

    • Author(s)
      N.Arai
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 1617-1622

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Aromatic Heterocyclic Ketones Catalyzed by the MsDPEN-Cp^*Ir(III)Complex.2010

    • Author(s)
      N.Utsumi
    • Journal Title

      HETEROCYCLES 80

      Pages: 141-147

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photosensitized Intramolecular Cyclization of Furan and Non-activated Alkene : Pathway Switching by the Substituent on the Furan Ring.2010

    • Author(s)
      N.Arai
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 1273-1275

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Cyanosilylation of α-Keto Esters Catalyzed by the[Ru(phgly)2(binap)]-C_6H_5OLi System.2010

    • Author(s)
      N.Kurono
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 1455-1459

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Hydrogenation of Ketones : Tactics to Achieve High Reactivity, Enantioselectivity, and Wide Scope.2010

    • Author(s)
      T.Ohkuma
    • Journal Title

      Proc.Jpn.Acad.Ser.B 86

      Pages: 202-219

    • NAID

      130000264074

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Practical Asymmetric Hydrogenation of 3-Quinuclidinone Catalyzed by the XylSkewphos/PICA-Ruthenium(II)Complex.2009

    • Author(s)
      K.Tsutsumi
    • Journal Title

      Org.Process Res.Dev. 13

      Pages: 625-628

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Active and Selective Semihydrogenation of Alkynes with the Palladiim Nanoparticle-Tetrabutylammonium Borohydride Catalyst System.2009

    • Author(s)
      J.Hori
    • Journal Title

      Adv.Synth.Catal. 351

      Pages: 3143-3149

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru錯体触媒によるケトン類の不斉水素化反応2009

    • Author(s)
      大熊毅
    • Journal Title

      触媒 51

      Pages: 577-582

    • NAID

      10026054989

    • Related Report
      2009 Annual Research Report
  • [Presentation] ルテニウム/リチウム複合錯体触媒を用いるアルジミン類の不斉ヒドロシアノ化反応2012

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、(横浜)
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] 新規なルテナビシクロ錯体触媒(RUCY)によるケトン類の高速かつ高選択的不斉水素化反応2012

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、(横浜)
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] α-アリールチオフェン類の新規分子内光環化反応2012

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、(横浜)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] ルテニウム錯体触媒によるN-アリールイミン類の不斉水素化反応2012

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、(横浜)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] 飽和複素環ケトン類の不斉水素化:触媒制御によるジアステレオ選択2012

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学、(横浜)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] Enantioselective Cyanosilylation of Ketones Catalyzed by Ruthenium Complex-LithiumSalts2012

    • Author(s)
      大熊毅
    • Organizer
      The 5th GCOE International Symposium
    • Place of Presentation
      北海道大学,札幌
    • Year and Date
      2012-02-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Enantioselective Cyanosilylation of Ketones Catalyzed by Ruthenium Complex-Lithium Salts2012

    • Author(s)
      大熊毅
    • Organizer
      The 5th GCOE International Symposium
    • Place of Presentation
      北海道大学、(札幌)
    • Year and Date
      2012-02-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Strecker-type Reaction of N-Protected Aldimines2012

    • Author(s)
      大熊毅
    • Organizer
      The 5th GCOE International Symposium
    • Place of Presentation
      北海道大学、(札幌)
    • Year and Date
      2012-02-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Conjugate Cyanation of α,β-Unsaturated Ketones Catalyzed by the Ruthenium Complex/C_6H_5OLi Systems2012

    • Author(s)
      大熊毅
    • Organizer
      The 5th GCOE International Symposium
    • Place of Presentation
      北海道大学、(札幌)
    • Year and Date
      2012-02-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Cyanation Catalyzed by Ru-Li Combined Systems2012

    • Author(s)
      大熊毅
    • Organizer
      The 5th GCOE International Symposium
    • Place of Presentation
      北海道大学、(札幌)(招待講演)
    • Year and Date
      2012-02-21
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Cyanation Catalyzed by the Chiral Ru-Li Combined Systems2011

    • Author(s)
      大熊毅
    • Organizer
      大阪大学基礎工学研究科講演会
    • Place of Presentation
      大阪大学、(豊中)(招待講演)
    • Year and Date
      2011-12-02
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Hydrocyanation Catalyzed by Ruthenium Complex/Lithium Salt System2011

    • Author(s)
      大熊毅
    • Organizer
      58th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      名古屋大学、(名古屋)
    • Year and Date
      2011-09-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Cyanation Using Ruthenium Complex/Lithium Salt Catalyst System2011

    • Author(s)
      大熊毅
    • Organizer
      The 2nd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会議場、(京都)
    • Year and Date
      2011-08-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] RUCY (Chiral Ruthenabicyclic Complexes) : Pre-Catalysts for Rapid, Enantioselective, and Wide-scope Hydrogenation of Ketones2011

    • Author(s)
      大熊毅
    • Organizer
      The 2nd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会議場、(京都)
    • Year and Date
      2011-08-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] ルテニウム錯体//C_6H_5OLi触媒系を用いるα,β-不飽和ケトン類の不斉共役シアノ化反応2011

    • Author(s)
      大熊毅
    • Organizer
      日本化学会北海道支部2011年夏季研究発表会
    • Place of Presentation
      室蘭工業大学、(室蘭)
    • Year and Date
      2011-07-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] ルテニウム錯体/C_6H_5OLi触媒系を用いるα,β-不飽和ケトン類の不斉共役シアノ化反応2011

    • Author(s)
      大熊毅
    • Organizer
      第23回万有札幌シンポジウム
    • Place of Presentation
      北海道大学、(札幌)
    • Year and Date
      2011-07-02
    • Related Report
      2011 Annual Research Report
  • [Presentation] Cu(I)触媒による逆電子要請分子内イミニウムエン反応を用いた4-アミノ-3-メチレンクロマン類の簡便合成2011

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第91春季年会2011
    • Place of Presentation
      神奈川大学横浜キャンパス(神奈川県)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] ルテニウム-リチウム複合錯体を用いるアルデヒド類の不斉ヒドロシアノ化反応2011

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第91春季年会2011
    • Place of Presentation
      神奈川大学横浜キャンパス(神奈川県)
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] ルテニウム錯体/c 6H 50Li触媒系を用いるα,β-不飽和ケトン類の不斉共役シアノ化反応2011

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第91春季年会2011
    • Place of Presentation
      神奈川大学横浜キャンパス(神秦川県)
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] BINAP/IPHAN-Ru (II)錯体触媒によるビシクロケトン類の不斉水素化反応2011

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第91春季年会2011
    • Place of Presentation
      神奈川大学横浜キャンパス(神奈川県)
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective Hydrocyanation of Aldehydes Catalyzed by Ruthenium-Lithium Combined Complexes.2010

    • Author(s)
      大熊毅
    • Organizer
      2010環太平洋国際化学会議(PACIFICHEM2010)
    • Place of Presentation
      ハワイコンベンションセンター(ワイキキ、米国)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] 医薬合成中間体「光学活性アルコール類」の高効率合成2010

    • Author(s)
      大熊毅
    • Organizer
      北海道大学工学系イノベーションフォーラム2010
    • Place of Presentation
      東京駅サピアタワー(東京都)
    • Year and Date
      2010-09-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Cyanosilylation of Aldehydes and a-Keto Esters with the Chiral Ru-Li Combined Catalysts.2010

    • Author(s)
      大熊毅
    • Organizer
      Joint Pre-Symposium on Organometallic Chemistry
    • Place of Presentation
      National Taiwan University, Taipei, Taiwan 招待講演
    • Year and Date
      2010-07-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Cyanosilylation of Aldehydes and α-Keto Esters Catalyzed by the Chiral Ru-Li Combined Systems2010

    • Author(s)
      大熊毅
    • Organizer
      22nd International Symposium on Chirality(ISCD-22)
    • Place of Presentation
      札幌コンベンションセンター,札幌
    • Year and Date
      2010-07-15
    • Related Report
      2011 Final Research Report
  • [Presentation] Asymmetric Cyanosilylation of Aldehydes and α-Keto Esters Catalyzed by the Chiral Ru-li Combined Systems2010

    • Author(s)
      大熊毅
    • Organizer
      22nd International Symposium on Chirality (ISCD-22)
    • Place of Presentation
      札幌コンベンションセンター(北海道) 招待講演
    • Year and Date
      2010-07-15
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Acylsilanes and Bicyclic Ketones Catalyzed by Diphosphine/Picolyl Amine-Ru(II) Complexes.2010

    • Author(s)
      大熊毅
    • Organizer
      22nd International Symposium on Chirality (ISCD-22)
    • Place of Presentation
      札幌コンベンションセンター(北海道)
    • Year and Date
      2010-07-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Cyanosilylation of a-Keto Esters Catalyzed by the [Ru (phgly) 2 (BINAP)]C 6H 5OLi System.2010

    • Author(s)
      大熊毅
    • Organizer
      22nd International Symposium on Chirality (ISCD-22)
    • Place of Presentation
      札幌コンベンションセンター(北海道)
    • Year and Date
      2010-07-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] ブラシと単純アルケンとの分子内光環化反応2010

    • Author(s)
      大熊毅
    • Organizer
      第22回万有札幌シンポジウム
    • Place of Presentation
      さっぽろ芸術文化の館(北海道)
    • Year and Date
      2010-07-03
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Ketones Catalyzed by ChiralRu(II)Complexes2010

    • Author(s)
      大熊毅
    • Organizer
      BIT's lst Annual World Congress of Catalytic Asymmetric Synthesis-2010(WCCAS-2010)
    • Place of Presentation
      Beijing International Convention Center(BICC) Beijing, China
    • Year and Date
      2010-05-20
    • Related Report
      2011 Final Research Report
  • [Presentation] Asymmetric Hydrogenation of Ketones Catalyzed by Chiral Ru(II) Complexes.2010

    • Author(s)
      大熊毅
    • Organizer
      BIT's 1^<st> Annual World Congress of Catalytic Asymmetric Synthesis-2010 (WCCAS-2010)
    • Place of Presentation
      Beijing International Convention Center (BICC), Beijing, China 招待講演
    • Year and Date
      2010-05-20
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Ketones with Chiral Ru(II) Catalysts.2010

    • Author(s)
      大熊毅
    • Organizer
      Organic Synthesis Symposium at BUCT (Beijing University of Chemical Teclmology)
    • Place of Presentation
      Beijing University of Chemical Technology (BUCT), Beijing China 招待講演
    • Year and Date
      2010-05-20
    • Related Report
      2010 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Acylsilanes and Bicylic Ketones Catalyzed by Diphosphine/Picolyl amine Ruthenium(II) Complexes.2010

    • Author(s)
      大熊毅
    • Organizer
      第21回日本医薬精密化学会議
    • Place of Presentation
      京都ガーデンパレス(京都府)
    • Year and Date
      2010-05-09
    • Related Report
      2010 Annual Research Report
  • [Presentation] MsDPEN-Cp^*イリジウム錯体触媒を用いる芳香属複素環状ケトシ類の不斉水素化反応2010

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第90春季年会(2010)
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] フランと単純アルケンとの光増感分子内環化反応2010

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第90春季年会(2010)
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] Ru(phgly)_2(binap)錯体を用いるα-ケトエステル類の斉シアノシリル化反応2010

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第90春季年会(2010)
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] Xylskewphos/PICA-ルテニウム錯体を触媒に用いる実用的な3-キヌクリジノンの不斉水素化反応2010

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第90春季年会(2010)
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] パラジウムナノ粒子-テトラブチルアンモニウムボロヒドリド触媒系によるアルキン類の高活性かつ高選択的な部分水素化反応2010

    • Author(s)
      大熊毅
    • Organizer
      日本化学会第90春季年会(2010)
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-26
    • Related Report
      2009 Annual Research Report
  • [Presentation] Asymmetric Hydrogenation of Acylsilanes and Bicylic Ketones Catalyzed by Diphosphine/Picolyl amine Ruthenium(II)Complexes2009

    • Author(s)
      大熊毅
    • Organizer
      北海道大学触媒化学研究センター 20周年記念国際シンポジウム
    • Place of Presentation
      札幌、北海道大学
    • Year and Date
      2009-12-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] 銅触媒によるラセミα-ヒドロキシエステル類の速度論分割の研究2009

    • Author(s)
      大熊毅
    • Organizer
      日本化学会北海道支部2009年夏季研究発表会
    • Place of Presentation
      苫小牧、苫小牧工業高等専門学校
    • Year and Date
      2009-07-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] フランと単純アルケンとの光増感Diels-Alder反応の開発研究2009

    • Author(s)
      大熊毅
    • Organizer
      日本化学会北海道支部2009年夏季研究発表会
    • Place of Presentation
      苫小牧、苫小牧工業高等専門学校
    • Year and Date
      2009-07-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] BINAP/DMAPEN-Ru(II)錯体触媒を用いるカルコン類の不斉水素化反応2009

    • Author(s)
      大熊毅
    • Organizer
      第21回 万有札幌シンポジウム
    • Place of Presentation
      札幌、北海道厚生年金会館
    • Year and Date
      2009-07-04
    • Related Report
      2009 Annual Research Report
  • [Presentation] 医薬合成鍵中間体「光学活性アミノアルコール類」の高効率合成2009

    • Author(s)
      大熊毅
    • Organizer
      ファーマiジャパン 研究成果発表フォーラム
    • Place of Presentation
      東京、東京ビッグサイト
    • Year and Date
      2009-07-02
    • Related Report
      2009 Annual Research Report
  • [Presentation] 不飽和化合物の不斉還元2009

    • Author(s)
      大熊毅
    • Organizer
      平成21年度前期(春季)有機合成化学講習会
    • Place of Presentation
      東京、日本薬学会長井記念館長井記念ホール
    • Year and Date
      2009-06-18
    • Related Report
      2009 Annual Research Report
  • [Book] Privileged Chiral Ligands and Catalysts (BINAP)2011

    • Author(s)
      T.Ohkuma
    • Total Pages
      53
    • Publisher
      Wiley-VCH
    • Related Report
      2011 Annual Research Report
  • [Book] Science of Synthesis : Stereoselective Synthesis 2 ; Stereoselective Reactions of Carbonyl and Imino Groups2010

    • Author(s)
      Noriyoshi Arai, Takeshi Ohkuma, Georg Thieme Verlag KG
    • Publisher
      Reduction of Carbonyl Compound : Hydrogenation
    • Related Report
      2011 Final Research Report
  • [Book] Science of Synthesis : Stereoselective Synthesis 2 ; Stereoselective Reactions of Carbonyl and Imino Groups (Reduction of Carbonyl Compound : Hydrogenation)2010

    • Author(s)
      N.Arai
    • Total Pages
      49
    • Publisher
      Georg Thieme Verlag KG
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://os-cp.eng.hokudai.acjp/os/Welcome.html

    • Related Report
      2011 Final Research Report
  • [Remarks] 国際シンポジウムの講演動画(学会発表(1))が公開された

    • URL

      http://www.mcip.hokudai.acjp/eng/4002video_lectures/video_lecture_asymmetric_cyana.html

    • Related Report
      2011 Final Research Report
  • [Remarks] 市販開始した不斉水素化触媒「RUCY-XylBINAP」がChemical & Engineering News 0ctoberl7,2011,pp.40-41に広告掲載さた。

    • URL

      http://www.cendigital.org/cendigital/20111017_sub?sub_id=51bdigXxgDUd#pg43

    • Related Report
      2011 Final Research Report
  • [Remarks] 本研究成果の一部がNano-scale robots work the irmagicのタイトルでNature Jobs, 22 September2011, p5(北海道大学特集号)に掲載された

    • URL

      http://www.nature.com/naturejobs/2011/110922/full/njO355.html#/nano-scale-robots-work-their-magic

    • Related Report
      2011 Final Research Report
  • [Remarks] 研究成果の一部が記事として「化学工業日報」2011年6月29日版に掲載された「超高速の不斉水素化触媒」

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.mcip.hokudai.ac.jp/eng/4002video_lectures/video_lecture_asymmetric_cyana.html

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミン化合物の製造方法2012

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2012-019742
    • Filing Date
      2012-02-01
    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アルコール化合物の製造方法2011

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2011-092511
    • Filing Date
      2011-04-18
    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アミノニトリル化合物およびその製造方法2011

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2011-221938
    • Filing Date
      2011-10-06
    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] ジアステレオ選択的にアリレコール化合物を製造する方法2010

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2010-279411
    • Filing Date
      2010-12-15
    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性アルコール化合物の製造方法2010

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2010-279412
    • Filing Date
      2010-12-15
    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性β-ケトニトリル化合物およびその製造方法2010

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2010-026762
    • Filing Date
      2010-02-09
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性シアノヒドリン化合物類2009

    • Inventor(s)
      大熊毅,黒野暢仁,植村真人,森浩幸
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2009-001112
    • Filing Date
      2009-11-12
    • Related Report
      2011 Final Research Report
  • [Patent(Industrial Property Rights)] 光学活性シアノヒドリン化合物類およびその製造方法2009

    • Inventor(s)
      大熊毅
    • Industrial Property Rights Holder
      北海道大学
    • Industrial Property Number
      2009-258736
    • Filing Date
      2009-11-12
    • Related Report
      2009 Annual Research Report

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

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