• Ag2O-catalysed nucleophilic isocyanation: selecive formation of less-stable benzyic isonitriles
    T. Yurino, Y. Tange, R. Tani, T. Ohkuma
    Org. Chem. Front. 2020 accepted (link)
  • Nucleophilic Isocyanation
    T. Yurino, T. Ohkuma
    ACS Omega 2020, 5, 4719–4724. (invited manuscript)
  • Selective Conversion of Benzylic Phosphates into Diarylmethanes through Al(OTf)3-Catalyzed Friedel–Crafts-type Benzylation
    T. Yurino, A. Hachiya, K. Suzuki, T. Ohkuma
    Eur. J. Org. Chem. 2020, 2020, 2225–2232
  • T. Yurino, H. Ece, T. Ohkuma
    Friedel–Crafts-type Allylation of Phenol Derivatives Catalyzed by Silyl Cyanometallates Generated In Situ
    Asian J. Org. Chem. 2020, 9557–560.


  • N. Arai, T. Ohkuma
    Stereoselective Preparation of Methylenecyclobutane-fused Angular Tetracyclic Spiroindolines via Photosensitized Intramolecular [2+2] Cycloaddition with Allene
    Tetrahedron Lett. 201960, 151252–151255.
  • N. Arai, Y. Okabe, T. Ohkuma
    Isomerization-Asymmetric Hydrogenation Sequence Converting Racemic β-Ylidenecycloalkanols into Stereocontrolled β-Substituted Cucloalkanols Using a Ru Catalytic System with Dual Roles
    Adv. Synth. Catal. 2019, 361, 5540-5547.
  • 大熊毅    
    触媒 2019, 61, 291–297
  • T. Yurino, R. Tani, T. Ohkuma
    Pd-Catalyzed Allylic Isocyanation: Nucleophilic N-Terminus Substitution of Ambident Cyanide
    ACS Catal. 20199, 4434–4440.
  • N. Arai, T. Ohkuma
    Stereoselective Construction of Methylenecyclobutane-Fused Indolines through Photosensitized [2+2] Cycloaddition of Allene-Tethered Indole Derivatives
    Org. Lett. 201921, 1506–1510.
  • 大熊毅
    「ジュッと音がする触媒を作りたい 高活性不斉水素化触媒開発奮闘記」
    化学と工業 201972–3, 259–261.
  • T. Ohkuma, N. Kurono, N. Arai
    Development of Asymmetric Reactions Catalyzed by Ruthenium Complexes with Two Kinds of Ligands (Award Accounts)
    Bull. Chem. Soc. Jpn. 2019, 92, 475–504.

    *Advertised in Twitter of CSJ(tweet 1, tweet 2


  • N. Utsumi, N. Arai, K. Kawaguchi, T. Katayama, T. Yasuda, K. Murata, T. Ohkuma*
    Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative-Ruthenium(II) Complexes
  • N. Arai, T. Ohkuma
    Construction of Unique Heterocyclic Frameworks by Photochemical Reaction of 5- and 6-Membered Heteroaromatics
    Heterocycles201896,  997–1035
    (invited review)
  • T. Ohkuma, N. Kurono, Y. Sakaguchi, K. Yamauchi, T. Yurino
    Enantioselective Cyanosilylation of Alkynyl Ketones Catalyzed by Combined Systems Consisting of Chiral Rughtnium(II) Complex and Lithium Phenoxide
    Adv. Synth. Catal. 20183601517–1522
  • N. Arai, T. Namba, K. Kawaguchi, Y. Matsumoto and T. Ohkuma
    Chemoselectivitiy Control in the Asymmetric Hydrogenation of γ- and δ-Keto Esters into the Hydroxy Esters or the Diols
    Angew. Chem. Int. Ed. 201857, 1386–1389


  • 大熊毅
    〔特集〕ノーベル賞受賞技術・理論の普及と化学工業の役割 「キラルテクノロジー:不斉水素化反応」
    化学工学 81(12), 666–669 (2017)
  • 新井則義、大熊毅
    現代科学 2017年12月号 18-23
  • 新井則義、大熊毅
    現代化学 2017年11月号 17–21
  • N. Arai, T. Ohkuma
    Photochemically Promoted Aza-Diels-Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
    J. Org. Chem. 2017, 827628–7636
  • N. Arai, H. Satoh, R. Komatsu, T. Ohkuma
    Double Asymmetric Hydrogenation of Linea β,β-Disubstituted α,β-Unsaturated Ketones into γ-Substituted Secondary Alcohols using a Dual Catalytic System
    Chem. Eur. J. 201723, 8806–8809 (inside cover picture)
  • 百合野大雅
    月刊化学 2017年2月号
  • T. Yurino
    Undirected Dehydrogenative Silylation of Aromatic C-H Bond
    J. Org. Synth. Chem. Jpn. 201775, 64-65


  • T. Ohkuma, N. Arai
    Advancement in Catalytic Asymmetric Hydrogenation of Ketones and Imines, and Development of Asymmetric Isomerization of Allylic Alcohols
    Chem. Rec. 201616, 2797–2815 (Invited Paper)
  • N. Arai, N. Onodera, T. Ohkuma
    Efficient chemoselective hydrogenation of organic azides catalyzed by palladium nanoparticles with alkyne-derived homogeneous supports
    Tetrahedron Lett. 201657, 4183—4186
  • 新井則義, 大熊 毅
    有機合成化学協会誌 2016, 74, 360–371
  • N. Kurono and T. Ohkuma,
    Catalytic Asymmertic Cyanation Reactions.
    ACS Catalysis, 2016, 6, 989–1023.
    (Invited Review)


  • 新井則義, 大熊 毅
    25.1.4 水素ガスを用いる還元法―触媒の調製と反応例
    有機合成実験法ハンドブック 第2版 (有機合成化学協会編)pp 852–859 (丸善) (2015)
  • N. Arai, N. Onodera, A. Dekita, J. Hori, and T. Ohkuma,
    Hydrogenation of Nitroarenes with Palladium Nanoparticles Stabilized by Alkyne Derivatives in Homogeneous Phase.
    Tetrahedron Letters, 2015, 56, 3913–3915.
  • N. Arai, M. Mizota, and T. Ohkuma,
    Stereoselective Preparation of Spiro[4.4] Cyclic Compounds by the Photochemical Activation of Oxazoles.
    Organic Letters, 2015, 17, 86–89.
  • N. Arai, M. Mizota, and T. Ohkuma,
    Novel Intramolecular Cyclization-Skeletal Reorganization of 2-Arylthiazoles under Photoirradiation.
    Heterocycles, 2015, 90, 607–616.
    (Isao Kuwajima’s Special Issues)


  • T. Ohkuma and N. Arai,
    “Phosphine, 1,1’-(1R)-[1,1’-binaphthalene]-2,2’-diylbis[bis(4-methylphenyl)-1 Phosphine, 1,1’-(1S)-[1,1’-binaphthalene]-2,2’-diylbis[bis(4-methylphenyl)-1” in e-EROS Encyclopedia of Reagents for Organic Synthesis, D. Crich, P. L. Fuchs, A. B. Charette, T. Rovis, Eds.; Wiley, 2014, pp 1-8.
  • Y. Sakaguchi, N. Kurono, K. Yamauchi, and T. Ohkuma,
    Asymmetric Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles with the Ru(phgly)2(binap)–CH3OLi Catalyst System.
    Organic Letters, 2014, 16, 808–811.
    (SYNFACTS 510 (2014))


  • N. Arai, Y. Saruwatari, K. Isobe, and T. Ohkuma,
    Asymmetric Hydrogenation of Quinoxalines, Benzoxazines, and a Benzothiazine Catalyzed by Chiral Ruthenabicyclic Complexes.
    Advanced Synthesis & Catalysis, 2013, 355, 2769–2774.
  • N. Arai, K. Sato, K. Azuma, and T. Ohkuma,
    Enantioselective Isomerization of Primary Allylic Alcohols into Chiral Aldehyde with the tol-binap/dbapen/Ruthenium(II) Catalyst.
    Angewandte Chemie, International Edition, 2013, 52, 7500–7504.
    (Selected as a Very Important Paper (VIP))
    (Highlighted at the Inside Cover)
    (SYNFACTS 1092 (2013))
    Isomerization-Inside Cover-AGC
  • N. Arai, H. Satoh, N. Utsumi, K. Murata, K. Tsutsumi, and T. Ohkuma,
    Asymmetric Hydrogenation of Alkynyl Ketones with η6-Arene/TsDPEN–Ruthenium(II) Catalyst.
    Organic Letters, 2013, 15, 3030–3033.
  • N. Kurono, T. Katayama, and T. Ohkuma,
    Preparation of Diastereomerically Pure and Mixed (S)-PhGly/BIPHEP/Ru(II) Complexes and Their Catalytic Behavior with Li2CO3 in Asymmetric Cyanosilylation of Benzaldehyde.
    Bulletin of the Chemical Society of Japan, 2013, 86, 577–582.
    (Selected Papers)


  • N. Arai, N. Utsumi, Y. Matsumoto, K. Murata, K. Tsutsumi, and T. Ohkuma,
    Asymmetric Hydrogenation of N-Arylimines Catalyzed by
    Advanced Synthesis & Catalysis, 2012, 354, 2089-2095.
    (SYNFACTS 1229 (2012))
  • T.Ohkuma and N. Kurono
    Asymmetric Cyanation with the Chiral Ru-Li Combined Catalysts.
    Synlett, 2012, 23, 1865-1881. (Invited Account Paper)
  • M. Uemura, N. Kurono, Y. Sakai, and T. Ohkuma,
    Enantioselective Cyanosilylation of Ketones with Amino Acids/BINAP/Ruthenium(II)-Lithium Phenoxide Catalyst Systems.
    Advanced Synthesis & Catalysis, 2012, 354, 2023-2030.
  • N. Arai, K. Tanaka, and T. Ohkuma,
    Novel Intramolecular Photocyclization of α-Arylthiophene Derivatives.
    Organic Letters., 2012, 14, 1488-1491.
  • M. Uemura, N. Kurono, and T. Ohkuma,
    Enantioselective Hydrocyanation of N-Protected Aldmines.
    Organic Letters, 2012, 14, 882-885.
    (SYNFACTS 525 (2012))


  • N. Kurono, K. Ohtsuga, M. wakabayashi, T. Kondo, H. Ooka, and T. Ohkuma,
    Kinetic Resolution of Racemic α-tert-Alkyl-α-hydroxy Esters by Enantiomer-Selective Carbamoylation.
    The Journal of Organic Chemistry, 2011, 76, 10312-10318.
  • M. Akashi, N. Arai, T. Inoue, and T. Ohkuma,
    Catalyst-Controlled Diastereoselection in the Hydrogenation of Heterocycloalkyl Ketones.
    Advanced Synthesis & Catalysis, 2011, 353, 1955-1960.
    (SYNFACTS 1336 (2011))
  • K. Matsumura, N. Arai, K. Hori, T. Sito, N. Sayo, and T. Ohkuma,
    chiral Ruthenabicyclic Complexes: Precatalysts for Rapid, Enantioselective, and Wide-Scope Hydrogenation of Ketones.
    Journal of the American Chemical Society, 2011, 133, 10696-10699.
    (SYNFACTS 968(2011))
  • Kuroo. N.; Nii, N.; Sakaguchi, Y.; Uemura, M.; T.; Ohkuma, T.,
    Asymmetric Hydrocyanation of α,β-Unsaturated Ketones into β-Cyano Ketones with
    the [Ru(phgly)2(binap)]/C6H5OLi Catalyst System.
    Angewandte Chemie, International Edition, 2011, 50 (24), 5541-5544.
    (SYNFACTS 866 (2011))
  • Kurono. N.; Yoshikawa. T.; Yamasaki. M.; Ohkuma. T.,
    Enantioselective Hydrocyanation of Aldehydes Catalyzed by [Li{Ru(phgly)2(binap)}]X(X=Cl, Br).
    Organic Letters, 2011, 13 (5), 1254-1257.
  • Arai. N.; Ohkuma. T.,
    Intramolecular iminium ene reaction with Cu(I) catalysis: facile formation of 4-amino-3-methylenechromans from O-propargyl salicyladehydes and dialkylamines.
    Tetrahedron, 2011, 67 (9), 1617-1622.


  • Utsumi. N.; Tsutsumi, K.; Watanabe, M.; Murata, K.: Arai, N.; Kurono, N.; Ohkuma, T.,
    Asymmetric hydrogenation of armatic heterocyclic ketones catalyzed by the MsDPEN-Cp^Ir(III)
    Heterocycles, 2010, 80(1), 141-147.
  • Ohkuma, T.,
    Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enanitioselectivity, and wide scope.
    Proceedings of the Japan Academy, Series B: Physical and Biological Sciences, 2010, 86(3), 202-219.
  • Kurono, N.; Uemura, M.: Ohkuma, T.,
    Asymmetric Cyanosilylation of α-Keto Esters Catalyzed by the [Ru(phgly)2(binap)]-C6H5OLi
    European Journal of Organic Chemistry. 2010, (8), 1455-1459.
  • Arai, N.; tanaka, K.; Ohkuma, T.,
    Photosensitized intramolecular cyclization of furan and non-activated alkene: pathway switching by the substituent on the furan ring.
    Tetrahedron Letters, 2010, 51 (9), 1273-1275.
  • Arai, N.: Akashi, M.: Sugizaki, S.; Ooka, H.; Inoue, T.; Ohkuma, T.;
    Asymmetric Hydrogenation of Bicyclic Ketones Catalyzed by BINAP/IPHAN-Ru(II) Complex.
    Organic Letters, 2010, 12 (15), 3380-3383.
    (SYNFACTS 1262 (2010))


  • Tsutsumi, K.; Katayama, T.; Utsumi, N;, Murata, K,; Arai, N.; Kurono, N.; Ohkuma, T.,
    Practical Asymmetric Hydrogenation of 3-Quinuclidinone Catalyzed by the XylSkewphos/PICA-Ruthenium(II) Complex.
    Organic Process Research & Development, 2009, 13 (3), 625-628.
  • Hori, J.; Murata, K.; Sugai, T.; Shinohara, H.; Noyori, R.; Arai, N.; Kurono, N.; Ohkuma, T.,
    Highly Active and Selective Semihydrogenation of Alkynes with the Palladium Nanoparticles-Tetrabutylammonuium Borohydride Catalyst System.
    Advanced Synthesis & Catalysis, 2009, 351 (18), 3143-3149.


  • Ooka, H.; Arai, N.; Azuma, K.; Kurono, N.; Ohkuma, T.,
    Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by the TolBINAP/DMAPEN-Ruthenium(II) Complex; A Significant Effect of N-Substituents of Chiral 1.2-Diamine Ligands on Enantioselectivity.
    The Journal of Organic Chemistry, 2008, 73 (22), 9084-9093.
  • Ohkuma, T.,
    Asymmetric hydrogenation of ketones using tailor-made catalyst.
    Organometallic News, 2008, (1), 8-13.
  • Kurono, N.; Kondo, T.; Wakabayahi, M.; Ooka, H.; Inoue, T.; Tachikawa, H.; Ohkuma, T.,
    Enantiomer-selective carbamoylation of racemic α-hydroxy gamma-Lactones with chiral Cu(II) Catalysts; an example of highly active Lewis acid catalyzed reaction.
    Chemistry, an Asian Journal, 2008, 3 (8-9), 1289-1297.
  • Kurono, N.; Arai, K.; Uemura, M.; Ohkuma, T.,
    [Ru(phgly)2(binap)]/Li2CO3: a highly active, robust, and enantioselective catalyst for the cyanosilylation of aldehydes.
    Angewandte Chemie, International Edition, 2008, 47 (35), 6643-6646.
    (SYNFACTS 1192 (2008))
  • Arai, N.; Suzuki, K.; Sugizaki, S.; Sorimachi, H.; Ohkuma, T.,
    Asymmetric hydrogenation of aromatic, aliphatic, and alpha, beta-unsaturated acyl silanes catalyzed by Tol-binap/Pica ruthenium(II) complexes: practical synthesis of optically active alpha-hydroxysilanes.
    Angewandte Chemie, International Edition, 2008, 47 (9), 1770-1773.
    (SYNFACTS 503 (2008))
  • Arai, N.; Azuma, K.; nii, N.; Ohkuma, T.,
    Highly enantioselective hydrogenation of arylvinyl ketones to allylic alcohols catalyzed by the tol-binap/dmapen ruthenium(II) complex.
    Angewandte Chemie, International Edition, 2008, 47 (39), 7457-7460.


  • Ohkuma, T.; Utsumi, N.; Watanabe, M.; Tsutsumi, K,; Arai, N.; Murata, K.,
    Asymmetric hydrogenation of alpha-hydroxy ketones catalyzed by MsDPEN-Cp^Ir(III) complex.
    Organic Letters, 2007, 9 (13), 2565-2567.
  • Ohkuma, T.; Tsutsumi, K.; Utsumi, N.; Arai, N.; Noyori, R.; Murata, K.,
    Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by η6-arene/TsDPEN-ruthenium(II) complexes.
    Organic Letters, 2007, 9 (2), 255-257.
  • Ohkuma, T.,
    Tailor-made catalysts for asymmetric hydrogenation of ketones.
    Yuki Gosei Kagaku Kyokaishi, 2007, 65 (11), 1070-1080.
  • Arai, N.; Ooka, H.; Azuma, K.; Yabuuchi, T.; Kurono, N.; Inoue, T.; Ohkuma, T.,
    General asymmetric hydrogenation of alpha-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex.
    Organic Letters, 2007, 9 (5), 939-941.


  • Ohkuma, T.; Utsumi, N.; Tsutsumi, K.; Murata, K.; Sandoval, C.; Noyori, R.,
    The Hydrogenation/Transfer Hydrogenation Network: Asymmetric Hydrogenation of Ketones with Chiral η6-Arene/N-Tosylethylenediamine-Ruthenium(II) Catalysts.
    Journal of the American Chemical Society, 2006, 128 (27), 8724-8725.
  • Kurono, N.; Suzuki, K.; Ohkuma, T.,
    Cyanosilylation of hetero-substituted ketones catalyzed by LiCl.
    Letters in Organic Chemistry, 2006, 3 (4), 275-277.

Reviews (Monographs)

  • T. Yurino, T. Ohkuma
    Atropisomerism and Axial Chirality, Lassaletta, J. M. Ed.; World Scientific
    Singapore, 2019, pp 149–247.
  • 大熊 毅,
    ファルマシア, 2015, 51, 295–299.
  • N. Arai and T. Ohkuma,
    Design of Molecular Catalysis for Achievement of High Turnover Number in Homogeneous Hydrogenation.
    Chem. Rec., 2012, 12, 284-289.
  • Ohkuma, T.; Kurono, N.,
    “BINAP” in Privileged Chiral Ligands and Catalysts, Zhou. Q.-L., Ed.; Wiley-VCH:
    Weinheim, 2011, pp 1-53.
  • Arai, N., Ohkuma, T.,
    “Reduction of Carbonyl Compound: Hydrogenation” in Science of Synthesis:
    Stereoselective Synthesis 2: Stereoselective Reactions of Carbonyl and lmino Groups,
    Molander, G. A., Ed.: Thieme: Stuttgart, 2010, pp 9-57.
  • Arai, N., Ohkuma, T.
    “Carbonyl Hydroboration” in Modern Reduction Methods, Anderson, P., Munslow, I., Eds.;
    Wiley-VCH: Weinheim, 2008, pp 159-181.
  • Ohkuma, T., Kitamura, M., Noyori, R.
    “Ligand Design for Catalytic Asymmetric Reduction” in New Frontiers in Asymmetric
    Catalysisi, Mikami K., Lautens, M. Eds.; Wiley: New Jersey, 2007, pp 1-32.
  • Ohkuma, T., Noyori, R.
    “Enantioselective Ketone and β-Keto Ester Hydrogenation (Including Mechanisms)” in The Handbook of Homogeneous Hydrogenation, de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH: Weinheim, 2007: Vol.3 pp 1105-1163.

Press Release

  • 化学工業日報 2020年6月11日 記事掲載
    「不斉水素化触媒を新開発 医薬品向け受託合成も活況」
  • 北海道新聞  2013年12月26日 記事掲載
    「みんなでサイエンス 同じ分子に異なる性質? 作り分けの技術を開発」
    (本学科学技術コミュニケーション教育研究部門CoSTEP 吉田ゆかり 特任准教授 執筆)
  • 日経産業新聞 2013年7月17日 記事掲載
    「アルデヒド、1回で合成  北海道大 新触媒で純度99%超」
  • 化学工業日報 2011年6月29日 記事掲載