Publications

Articles

2020

  • 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, 9,  557–560.

2019

  • N. Arai, T. Ohkuma
    Stereoselective Preparation of Methylenecyclobutane-fused Angular Tetracyclic Spiroindolines via Photosensitized Intramolecular [2+2] Cycloaddition with Allene
    Tetrahedron Lett. 2019, 60, 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    
    ルテニウム錯体触媒を用いるイミン類の不斉水素化反応 
    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. 2019, 9, 4434–4440.
  • N. Arai, T. Ohkuma
    Stereoselective Construction of Methylenecyclobutane-Fused Indolines through Photosensitized [2+2] Cycloaddition of Allene-Tethered Indole Derivatives
    Org. Lett. 2019, 21, 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 2019, 72–3, 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）

2018

  • 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
    ChemCatChem, 2018, 10, 3955–3959
  • N. Arai, T. Ohkuma
    Construction of Unique Heterocyclic Frameworks by Photochemical Reaction of 5- and 6-Membered Heteroaromatics
    Heterocycles, 2018, 96,  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. 2018, 360, 1517–1522
  • 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. 2018, 57, 1386–1389

2017

  • 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
    あの身近な化合物はこうやってつくられた
    現代科学　2017年12月号 18-23
  • 新井則義、大熊毅
    有機化合物のつくりかた事始め
    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, 82, 7628–7636
  • 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. 2017, 23, 8806–8809 (inside cover picture)
  • 百合野大雅
    水から水素を取り出して”移し替える”
    月刊化学 2017年2月号
  • T. Yurino
    Undirected Dehydrogenative Silylation of Aromatic C-H Bond
    J. Org. Synth. Chem. Jpn. 2017, 75, 64-65

2016

  • T. Ohkuma, N. Arai
    Advancement in Catalytic Asymmetric Hydrogenation of Ketones and Imines, and Development of Asymmetric Isomerization of Allylic Alcohols
    Chem. Rec. 2016, 16, 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. 2016, 57, 4183—4186
  • 新井則義, 大熊　毅
    光による分子活性化を利用した含ヘテロ多環系骨格構築手法の開発
    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)

2015

  • 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)

2014

  • 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))

2013

  • 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)

2012

  • 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))

2011

  • 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.

2010

  • 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)
    complex.
    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
    System.
    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))

2009

  • 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.

2008

  • 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.

2007

  • 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.

2006

  • 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,
    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.
    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
    「超高速の不斉水素化触媒」