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研究業績

教員の全業績はこちらへ

原著論文（金沢大学における業績）

2024年

  1. Nagae, T.; Fujita, Y.; Tsuchida, T.; Kamo, T.; Seto, R.; Hamada, M.; Aoyama, H.; Sato-Tomita, A.; Fujisawa, T.; Eki, T.; Miyanoiri, Y.; Ito, Y.; Soeta, T.; Ukaji, Y.; Unno, M.; Mishima, M.; Hirose, Y. Green/Red Light-Sensing Mechanism in the Chromatic Acclimation Photosensor. Sci. Adv. 2024, 10, eadn8386. DOI: 10.1126/sciadv.adn8386
  2. Maeba, T.; Hirata, K.; Kotoku, M.; Seki, N.; Maeda, K.; Hirashima, S.; Yamanaka, H.; Sakai, T.; Obika, S.; Hori, A.; Hara, Y.; Noji, S.; Suwa, Y.; Yokota, M.; Fujioka, S.; Yamaguchi, T.; Katsuda, Y.; Hata, T.; Miyagawa, N.; Arita, K.; Nomura, Y.; Taniguchi, T.; Asahina, K.; Aratsu, Y.; Naka, Y.; Adachi, T.; Nomura, A.; Akai, S.; Oshida, S.-I.; Pai, S.; Crowe, P.; Bradley, E.; Steensma, R.; Tao, H.; Fenn, M.; Babine, R.; Li, X.; Thacher, S.; Soeta, T.; Ukaji, Y.; Shiozaki, M. Discovery and SAR of JTE-151: A Novel RORγ Inhibitor for Clinical Development. J. Med. Chem. 2024, 67, 952–970. DOI: 10.1021/acs.jmedchem.3c01933
  3. Soeta, T. ; Yao, S.; Sugiyama, H.; Ukaji, Y. Silylacetate-Promoted Addition Reaction of Isocyanides to Nitrones: Effective Synthesis of C(1)-Carboxamide Derivatives. Org. Biomol. Chem. 2024, 22, 1619–1623. DOI: 10.1039/d3ob01777j
  4. Suga, T.; Ukaji, Y. Molecular Transformations Based on Homolytic Cleavage of Alcohol and Ether C–O Bonds. J. Synth. Org. Chem., Jpn. 2024, 82, 697–708. DOI: 10.5059/yukigoseikyokaishi.82.697
  5. Suga, T.; Takada, R.; Sakamoto, M. Ukaji, Y. Directing-Group-Assisted Non-Strained Ether C–O Bond Homolysis Mediated by Low-Valent Titanium. Org. Lett. 2024, 26, 2315–2310. DOI: 10.1021/acs.orglett.4c00590
  6. Suga, T.; Kondo, M.; Takahashi, Y.; Ukaji, Y. Nickel-Catalyzed Cross-Coupling Between Benzyl Alcohols and Alkenyl Triflates Assisted by Titanium-Mediated Radical C–O Bond Cleavage. Bull. Chem. Soc. Jpn. 2024, 97, uoad003. DOI: 10.1093/bulcsj/uoad003

2023年

  1. Ohno, H.; Takahashi, R.; Suga, T.; Soeta, T.; Ukaji, Y. Divergent transformation of C,N-cyclic-N‘-acyl azomethine imines by reaction with diazo compounds. Org. Biomol. Chem. 2023, 21, 7891–7894. DOI: 10.1039/d3ob01165h
  2. Sato, Y.; Ukei, T.; Tsugeno, H.; Suga, T.; Soeta, T.; Ukaji, Y. Asymmetric Hetero-Diels-Alder Reaction of 4-Phenyl-1,2,4-triazole-3,5-dione with 2,4-Dienyl Carboxylic Acids. Synthesis, 2023, 55, 3342–3348.  DOI: 10.1055/a-2131-0116
  3. Soeta, T.; Kurobe, S.; Nirei, Y.; Kurokawa, N.; Wei, W.; Yurtsever, A.; Fukuma, T.; Ukaji, Y. Molecular Assembly and Gelating Behavior of (L)-Alanine Derivatives. Chem. Eur. J. 2023, 29, e202300455. DOI: 10.1002/chem.202300455
  4. Suga, T.; Miki, C.; Ukaji, Y. From-Neutral-to-Neutral Reductive Radical Coupling of Non-Activated Alcohols and Styrenes. ChemistryEurope 2023, 1, e202300033. DOI: 10.1002/ceur.202300033

2022年

  1. Sakurai, T.; Yano, T.; Suga, T.; Soeta, T.; Ukaji, Y. Formal Methylene Insertion into the C–H Bond of α-Carbonyl Aldonitrones with Dimethylsulfoxonium Methylide. Bull. Chem. Soc. Jpn. 2022, 95, 1518–1520. DOI: 10.1246/bcsj.20220212
  2. Wei, Q.; Ii, H.; T. Suga, T.;Soeta, T.; Maeda, H.; Ukaji, Y. Hydroxy Group-Directed Diastereoselective Paternó–Büchi Reaction between Arylglyoxylates and Furfuryl Alcohols. Chem. Lett. 2022, 51, 1143–1145. DOI: 10.1246/cl.220437
  3. Suga, T.; Takada, R.; Shimazu, S.; Sakata, M.; Ukaji, Y. Highly (E)-Selective Trisubstituted Alkene Synthesis by Low-Valent Titanium-Mediated Homolytic Cleavage of Alcohol C–O Bond. J. Org. Chem. 2022, 87, 7487–7493. DOI: 10.1021/acs.joc.2c00246
  4. Suga, T.; Takahashi, Y.; Miki, C.; Ukaji, Y. Direct and Unified Access to Carbon Radicals from Aliphatic Alcohols by Cost-Efficient Titanium-Mediated Homolytic C–OH Bond Cleavage. Angew. Chem. Int. Ed. 2022, 61, e202112533. DOI: 10.1002/anie.202112533

2021年

  1. Soeta, T.; Kaneta, K.; Hatanaka, Y.; Ida, T.; Ukaji, Y. N-Heterocyclic Carbene-Catalyzed Chemoselective Monoacylation of 1,n-Linear Diols. Org. Lett. 2021, 23, 8138–8142. DOI: 10.1021/acs.orglett.1c02749
  2. Suga, T.; Nakamura, M.; Takada, R.; Ukaji, Y. Conjugate Addition of Acetal-Derived Benzyl Radicals Generated from Low-Valent Titanium-Mediated C–O Bond Cleavage. Bull. Chem. Soc. Jpn. 2021, 94, 1258–1260. DOI: 10.1246/bcsj.20200364

2020年

  1. Soeta, T.; Ukaji, Y.Development of multi-functional NHC Catalysts bearing pyridine moiety: Application to Catalytic Asymmetric Reactions. J. Synth. Org. Chem., Jpn. 2020, 78, 338–349. DOI: 10.5059/yukigoseikyokaishi.78.338
  2. Hasegawa, M.; Suga, T.; Soeta, T.; Ukaji, Y. Synthesis of 3,6-Duhydro-2H-1,2-oxazines via Dimethylsulfoxonium Methylide to a,b-Unsaturated Nitrones. J. Org. Chem. 2020, 85, 11258–11264. DOI: 10.1021/acs.joc.0c01349
  3. Suga, T.; Takahashi, Y.; Ukaji, Y. One-Shot Radical Cross Coupling Between Benzyl Alcohols and Alkenyl Halides Using Ni/Ti/Mn System, Adv. Synth. Catal. 2020, 362, 5622–5626. VIP article. DOI: 10.1002/adsc.202000945

2019年

  1. Takahashi, R.; Phan, N. H. T.; Suga, T.; Soeta, T.; Ukaji, Y. Synthesis of Optically Acitve γ-Lactams by Palladium Catalyzed Asymmetric Dicarbonylation Reaction of N-Arylsufonyl Homoallylic Amines. Heterocycles 2019, 98, 1044−1054. DOI: 10.3987/com-19-14112

2018年

  1. Soeta, T.; Hatanaka, Y.; Ishizaka, T.; Ukaji, Y.Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed Addition of Diethylzinc to Nitroalkenes. Tetrahedron, 2018, 74, 4601–4605. DOI: 10.1016/j.tet.2018.07.030
  2. Soeta, T.; Ohashi, N.; Kobayashi, T.; Sakata, Y.; Suga, T.; Ukaji, Y. Synthesis of Sterically Fixed Phytochrome Chromophore Derivatives bearing a 15E-anti fixed or 15E-fixed CD-Ring Component. J. Org. Chem.2018, 83, 10743–10748. DOI: 10.1021/acs.joc.8b01252
  3. Soeta, T.; Matsuzaki, S.; Ukaji, Y. Phenylphosphinic Acid-Promoted Addition of Isocyanides to 1-Methoxyisochroman Derivatives. Heterocycles, 2018, 97, 355–364. DOI: 10.3987/com-18-s(t)23
  4. Soeta, T.; Matsumoto, A.; Ukaji, Y. Development of a Synthetic Method for Multifunctionalized Pyrroles Using Isocyanide Dichloride as a Key Intermediate J. Org. Chem. 2018, 83, 4831–4834. DOI: 10.1021/acs.joc.8b00185
  5. Suga, T.; Ukaji, Y. Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant. Org. Lett. 2018, 20, 7846–7850. Top 10 most read article in Dec. 2018. DOI: 10.1021/acs.orglett.8b03367
  6. Suga, T.; Shimazu, S.; Ukaji, Y. Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources. Org. Lett., 2018, 20, 5389–5392. Highlighted in Knochel. P.; Graßl, S. Synfacts 2018, 14, 1184, Organic Chemistry Portal, etc. DOI: 10.1021/acs.orglett.8b02305

2017年

  1. Soeta, T.; Mizuno, S.; Hatanaka, Y.; Ukaji, Y. Asymmetric cross-benzoin condensation promoted by chiral triazolium precatalyst bearing a pyridine moiety. Tetrahedron, 2017, 73, 3430–3437. DOI: 10.1016/j.tet.2017.05.001
  2. Soeta, T.; Matsumoto, A.; Sakata, Y.; Ukaji, Y. Deveopment of a One-Pot Synthetic Method for Multifunctional Oxazole Derivatives Using Isocyanide Dichloride. J. Org. Chem. 2017, 82, 4930–4935. DOI: 10.1021/acs.joc.7b00296
  3. Tong, T. M. T.; Soeta, T.; Suga, T.; Kawamoto, K.; Hayaahi, Y.; Ukaji, Y. Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines. J. Org. Chem. 2017, 82, 1969–1976. DOI: 10.1021/acs.joc.6b02816
  4. Hasegawa, M.; Nomoto, A.; Suga, T.; Soeta, T.; Ukaji, Y. Palladium-Catalyzed C-H Alkenylation of C-Aryl Nitrones. Chem. Lett. 2017, 46, 46–47. DOI: 10.1246/cl.160821

2016年

  1. Soeta, T.; Shitaya, S.; Okuno, T.; Fujinami, S.; Ukaji, Y.Effective synthesis of Benzothiophenes by [4+1] Cycloaddition of 2-Mercaptobenzaldehyde Derivatives with Isocyanides. Tetrahedron 2016, 72, 7901–7905. DOI: 10.1016/j.tet.2016.09.054
  2. Phan, N. H. T.; Furuya, T.; Soeta, T.; Ukaji, Y. Palladium-Catalyzed Intermolecular Alkoxy-Alkoxycarbonylation of Vinylphenols in the Presence of Copper Salt: Unexpected Cooperative Effect of Tin Salt. Chem. Lett. 2016, 45, 1431–1433. DOI: 10.1246/cl.160804
  3. Soeta, T.; Takashita, S.; Sakata, Y.; Ukaji, Y. Ugi-type Multicomponent Reaction of Nitrile Imines, Isocyanides, and Isocyanates: Effective Synthesis of 1,2,4-Triazinedione Derivatives. Asian J. Org. Chem. 2016, 5, 1041–1047. DOI: 10.1002/ajoc.201600191
  4. Watanabe, Y.; Sakai, T.; Maeda, H.; Segi, M.; Soeta, T.; Ukaji, Y. Magnesium-Alkoxide Directed Photoaddition of Tetrahydrofyrans to γ,γ-Disubstituted Allylic Alcohols. Heterocycles 2016, 93, 833–844. DOI: 10.3987/com-15-s(t)65
  5. Soeta, T.; Takashita, S.; Sakata, Y.; Ukaji, Y. Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides. Org. Biomol. Chem. 2016, 694–700. DOI: 10.1039/c5ob02032h
  6. Soeta, T.; Ishizaka, T.; Ukaji, Y. Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines. J. Org. Chem. 2016, 81, 2817–2826. DOI: 10.1021/acs.joc.6b00093
  7. Seo, D.; Soeta, T.; Sakurai, T.; Sakurai, H.; Setif, P. Pre-steady-state kinetic studies of redox reactions catalysed by Bacillus subtilis ferredoxin-NADP(+) oxidoreductase with NADP(+)/NADPH and ferredoxin. Biochim. Biophys. Acta. 2016, 1857, 678–687. DOI: 10.1016/j.bbabio.2016.03.005

2015年

  1. Soeta, T.; Matsuzaki, S.; Ukaji, Y. A One-Pot O-Sulfinative Passerini/Oxidation Reaction: Efficient Synthesis of a-(Sulfonyloxy)amide. J. Org. Chem. 2015, 80, 3688–3694. DOI: 10.1021/acs.joc.5b00131
  2. Sakata, R.;Soeta, T.; Ukaji, Y. One-Carbon Homologation of Pyrrole Carboxaldehyde via Wittig Reaction and  Mild Hydrolysis of Vinyl Ether － Toward the Synthesis of a Sterically Locked Phytochrome. Heterocycles 2015, 91, 593–603. DOI: 10.3987/com-14-13157
  3. Soeta, T.; Ukaji, Y. Development of New Synthetic Methods for Heterocycles Utilizing 1,3-Dipoles. J. Synth. Org. Chem., Jpn. 2015, 73, 65–75. DOI: https://doi.org/10.5059/yukigoseikyokaishi.73.65
  4. Tanaka, Y.; Iwamoto, R. Sakata, R.; Soeta, T.; Endo, K.; Fujinami, S.; Inomata, K.; Ukaji, Y. Regioselective Introduction of Substituents to the meso-Position of Pyrromethanone derivative – Application to the Synthesis of Sterically Fixed Phytochrome Chromophore Anchored to the C15 meso-Position. Heterocycles 2015, 91, 883–892. DOI: 10.3987/com-14-s(k)97
  5. Kurosawa, F.; Nakano, T. Soeta, T.; Endo, K.; Ukaji, Y. (Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2]-Wittig Rearrangement. J. Org. Chem. 2015, 80, 5696–5703. DOI: 10.1021/acs.joc.5b00647

2014年

  1. Soeta, T.; Ishizaka, T.; Tabatake, Y.; Ukaji, Y. Chiral NHC Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents. Chem. Eur. J. 2014, 20, 16773–16778. DOI: 10.1002/chem.201404241
  2. Soeta, T.; Ohgai, T.; Sakai, T.; Fujinami, S.; Ukaji, Y. Ring Enlargement Reaction of C,N-Cyclic-N’-Acyl Azomethine Imines with Sulfonium Ylide: An Efficient Synthesis of 3-Benzazepine Derivatives. Org. Lett.2014, 16, 4854–4857. DOI: 10.1021/ol502347n
  3. Soeta, T.; Miyamoto, Y.; Fujinami, S.; Ukaji, Y. Lewis Acid Catalyzed [3+1+1] Cycloaddition of Azomethine Ylides with Isocyanides. Tetrahedron 2014, 70, 6623–6629. DOI: 10.1016/j.tet.2014.06.18
  4. Soeta, T.; Tamura, K.; Ukaji, Y. [4+1] Cycloaddition of N-Acyl Imine Derivatives with Isocyanides: Efficient Synthesis of 5-Aminooxazoles and 5-Aminothiazoles. Tetrahedron 2014, 70, 3005–3010. DOI: 10.1016/j.tet.2014.03.016
  5. Soeta, T.; Matsuzaki, S.; Ukaji, Y. A One-Pot O-Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized a-(Phosphinyloxy)amide Derivatives. Chem. Eur. J.2014, 20, 5007–5012. DOI: 10.1002/chem.201304618
  6. Yoshida, M.; Sassa, N.; Kato, T.; Fujinami, S.; Soeta, T.; Inomata, K.; Ukaji, Y. Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines. Chem. Eur. J.2014, 20, 2058–2064. DOI: 10.1002/chem.201302889
  7. Soeta, T.; Ukaji, Y. Carboxylic Acid Free Novel Isocyanide Based Reaction. Chem. Rec. 2014, 14, 101–116. DOI: 10.1002/tcr.201300021

2013年

  1. Sakai, T.; Soeta, T.; Endo, K.; Fujinami, S.; Ukaji, Y.Magnesium–Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin. Org. Lett. 2013, 15, 2422–2425. DOI: 10.1021/ol400898p
  2. Soeta, T.; Tabatake, Y.; Fujinami, S.; Ukaji, Y. N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Aldehydes with Carbodiimides under Aerobic Conditions: Efficient Synthesis of N-Acylureas. Org. Lett. 2013, 15, 2088–2091. DOI: 10.1021/ol400672c
  3. Soeta, T.; Tamura, K.; Ukaji, Y. Three-Components Reaction of C,N-cyclic N’-acyl azomethine imines, Isocyanide, and Azide Compounds: Effective Synthesis of 1,5-Disubstituted Tetrazoles bearing Tetrahydeoisoquinoline Skeletons. Org. Biomol. Chem. 2013, 11, 2168–2174. DOI: 10.1039/c3ob27297d
  4. Miyamoto, Y.; Wada, N.; Soeta, T.; Fujinami, S.; Inomata, K.; Ukaji, Y. One-pot Stereoselective Syntheses of 2-Acylaziridines and 2-Acylpyrrolidines from N-(Propargylic)hydroxylamines. Chem. Asian. J. 2013, 8, 824–831. DOI: 10.1002/asia.201201180
  5. Nakano, T.; Soeta, T.; Endo, K.; Inomata, K.; Ukaji, Y. Stereoselective Synthesis of (2Z,4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2-butenyl Benzoates. J. Org. Chem. 2013, 78, 12654–12661. DOI: 10.1021/jo402272r

2012年

  1. Takahashi, K.; Iwamoto, R.; Sakata, R.; Soeta, T.; Inomata, K.; Ukaji, Y. Direct Oxidation of 4-Methylpyrrole-2-carboxylates with DDQ in the presence of a Glycol. Heterocycles 2012, 86, 1031–1038. DOI: 10.3987/com-12-s(n)126
  2. Soeta, T.; Tabatake, Y.; Ukaji, Y. Asymmetric Intramolecular Stetter Reaction Catalyzed by the Chiral Triazolium Precatalyst Bearing a Pyridine Moiety. Tetrahedron 2012, 49, 10188–10983. DOI: 10.1016/j.tet.2012.09.095}
  3. Soeta, T.; Fujinami, S.; Ukaji, Y. Chlorosilane-Promoted Addition Reaction of Isocyanide to 3,4-Dihydroisoquinoline N-Oxides.J. Org. Chem. 2012, 77, 9878–9883. DOI: 10.1021/jo301791m
  4. Ohashi, R.; Wakabayashi, G.; Mizuno, M.; Soeta, T.; Hashimoto, M. Yamamura, K. Molecular Dynamics of Octyl Urea Crystals Analyzed by Solid-State NMR. Chem. Lett. 2012, 41, 1433–1435. DOI: 10.1246/cl.2012.1433
  5. Sakai, T.; Soeta, T.; Inomata, K.; Ukaji, Y. Strecker-type reaction of nitrones using cyanohydrin. Bull. Chem. Soc. Jpn. 2012, 85, 231-235. DOI: 10.1246/bcsj.20110270
  6. Soeta, T.; Tamura, K.; Ukaji, Y. [5+1] Cycloaddition of C,N-Cyclic N’-Acyl Azomethine Imines with Isocyanides. Org. Lett. 2012, 14, 1226–1229. DOI: 10.1021/ol2034542
  7. Soeta, T.; Tabatake, Y.; Inomata, K.; Ukaji, Y. Asymmetric Benzoin Condensation Promoted by Chiral Triazolium Precatalyst Bearing a Pyridine Moiety. Tetrahedron 2012, 68, 894–899. DOI: 10.1016/j.tet.2011.11.028

2011年

  1. Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. Borinic Acid Catalyzed a-Addition of Isocyanide with Aldehydes and Water. Tetrahedron Lett. 2011, 52, 2557–2559. DOI: 10.1016/j.tetlet.2011.03.032

2010年

  1. Soeta, T.; Kojima, Y.; Ukaji, Y.; Inomata, K. O-Silylative Passerini Reaction: A New One-Pot Synthesis of a–Siloxyamides. Org. Lett. 2010, 12, 4341–4343. DOI: 10.1021/ol101763w

著書

(1)“Methods and Applications of Cycloaddition Reactions in Organic Syntheses.” Chap.11,Development of New Methods for the Construction of Heterocycles Based on Cycloaddition Reaction of 1,3-Dipoles. Takahiro Soeta, Yutaka Ukaji. 2013. Wiley

(2) Comprehensive Chirality,” Chap. 4.06. Acetogenin (Polypriopionate) Derived Auxiliaries/Tartaric Acid. Takahiro Soeta, Yutaka Ukaji. 2011, Elsevier.

特許

(1) Preparation of phenyloxalamide derivatives for use as CD4 mimetics. Joseph Sodroski, Navid Madani, Arne Schon, Judith M Londe La, Joel R Courter, Takahiro Soeta, Danny Ng, Ernesto Freire, Amos B Smith III. PCT Int. Appl. (2010), 130pp. CODEN: PIXXD2 WO 2010053583 A220100514

(2) Sodroski, J.; Lalonde, J. M.; Smith, A. B., III; Kwong, P. D.; Kwon, Y. D.; Jones, D. M.; Sun, A. W.; Courter, J. R.; Soeta, T.; Kobayashi, T.; Princiotto, A. M.; Wu, X.; Mascola, J. R.; Schon, A.; Freire, E.; Madani, N.; Le-Khac, M.; Hendrickson, W. A. Preparation of indene compounds as CD4-mimetic inhibitors of HIV-1 entry and methods of therapeutic use thereof. WO2013090696A1, 2013.

学会発表

添田研究室｜金沢大学大学院 自然科学研究科 物質化学専攻｜金沢大学 理工研究域 物質化学系 化学コース 有機化学研究分野
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