Grant-in-Aid for Scientific Research on Innovative Areas FY2017-2021Hybrid Catalysis

Keiji Maruoka » Japanese

Affiliation Graduate School of Pharmaceutical Science, Kyoto University
Position Professor
Contact Email
HP http://kuchem.kyoto-u.ac.jp/yugo/orgcat/english/index.html
Speciality Organocatalytic Chemistry
Keyword Organocatalyst, New Synthetic methodology, Metal Catalyst, Radical Chemistry
Institute The Chemical Society of Japan, Synthetic Organic Chemistry, Japan, The Pharmaceutical Society of Japan, The Japanese Society for Process Chemistry, American Chemical Society

Abstract

◆Project Title
Development of Highly Selective Domino-Type Reactions using High-Performance Hybrid Catalyst Systems

◆Research Outline
Design of new catalysts and development of new synthetic reactions in an environmental manner are required in recent years. For this reason, incorporating the advantages of in vivo systems into organic synthesis would be certainly one of the most powerful strategies. For example, in biological systems, it is easy to activate organic molecules by multicatalytic reactions involving multiple enzymes (biocatalysts) and synthesize complex natural products at once. However, it is extremely difficult to do the same transformations artificially. If it is possible to extract functions such as substrate recognition and activation without using macromolecules such as enzymes and reproduce with small Lewis acidic metal catalysts, metal complex catalysts or organocatalysts for precise organic synthesis, a new direction will be given to the catalyst design. In this research, we aim to develop new domino-type synthetic transformations by designing "high-performance hybrid catalysts" in which multiple catalysts act with independent functions cooperatively.

Achievement

Printer friendly view

Original papers

  • "Design of New Amino Tf- Amide Organocatalysts: Environmentally Benign Approach to Asymmetric Aldol Synthesis
"
    Lee, H.-J.; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; *Maruoka, K.
    Synlett, 3/2019, 30, 401-404
  • "Generation of Alkyl Radicals from Alkylsilyl Peroxides and Their Applications to C-N or C-O Bond Formations
"
    Sakurai, S.; Kato, T.; Sakamoto, R.; *Maruoka, K.
    Tetrahedron, 1/2019, 75, 172-179
  • "Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Brønsted Acidic NO2+ Generation
"
    Juarez-Ornelas, K. A.; Jimenez-Halla, J. O. C.; Kato, T.; *Solorio-Alvarado, C. R.; *Maruoka, K.
    Org. Lett., 3/2019, 21, 1315-1319
  • "Enantioselective Alkynylation of Isatin Derivatives Using a Chiral Phase-TransferTransition- Metal Hybrid Catalyst System
"
    Paria, S.; Lee, H.-J.; *Maruoka, K.
    ACS Catal., 3/2019, 9, 2395-2399
  • "Benzimidazole Tethered Pyrrolo[3,4-b]quinoline with Broad-spectrum Activity Against Fungal Pathogens
"
    Villa, P.; *Arumugam, N.; Almansour, A. I.; Kumar, R. S.; Mahalingam, S. M.; Maruoka, K.; *Thangamani, S.
    Bioorg. Med. Chem. Lett., 3/2019, 29, 729-733
  • "Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations
"
    Paria, S.; Kang, Q.-K.; Hatanaka, M.; *Maruoka, K.
    ACS Catal., 1/2019, 9, 78-82
  • "Practical Synthesis of Four Different Pseudoenantiomeric Organocatalysts with Both Cis- and Trans-Substituted 1,2-Cis-cyclohexanediamine Structures from a Common Intermediate"
    
 Lee, H.-J.; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; *Maruoka, K.
    Tetrahedoron, 9/2018, 74, 5263-5269
  • "BF3-Catalyzed Synthesis of Cyclic Carbamates from Boc-Protected Aminals and Alkynes
"
    *Kano, T.; Yasumoto, K.; *Maruoka, K.
    Asian J. Org. Chem., 8/2018, 7, 1575-1578
  • "The Radical Acylarylation of N-Arylacrylamides with Aliphatic Aldehydes Using the Photolysis of Hypervalent Iodine(III) Reagents
"
    Sakamoto, R.; Hirama, N.; *Maruoka, K.
    Org. Biomol. Chem., 7/2018, 16, 5412-5415
  • "Enantioselective Alkylation of N-Arylhydrazones Derived from α-Keto Esters and Isatin Derivatives through Asymmetric Phase-Transfer Catalysis
"
    Kang, Q.-K.; Selvakumar, S.; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; *Maruoka, K.
    Chemistry–Asian J., 7/2018, 13, 1780-1783
  • "Synthesis of 1-Aminoindenes through Aza-Prins-Type Cyclization"
    
 Bai, J.-F.; Yasumoto, K.; *Kano, T.; *Maruoka, K.
    Chemistry–Eur. J., 7/2018, 24, 10320-10323
  • "Transition-Metal-Free Direct C-H Silylation of Electron-Deficient Heteroarenes with Hydrosilanes via a Radical Mechanism
"
    Sakamoto, R.; Nguyen, B.-N.; *Maruoka, K.
    Asian J. Org. Chem., 7/2018, 7, 1085-1088
  • "Phase-transfer-catalysed Asymmetric Synthesis of 2,2-Disubstituted 1,4-Benzoxazin-3-ones
"
    Pawliczek, M.; Shimazaki, Y.; Kimura, H.; Oberg, K. M.; Zakpur, S.; Hashimoto, T.; *Maruoka, K.
    Chem. Commun., 6/2018, 54, 7078-7080
  • "Indanol-Based Chiral Organoiodine Catalysts for Enantioselective Hydrative Dearomatization
"
    Hashimoto, T.; Shimazaki, Y.; Omatsu, Y.; *Maruoka, K.
    Angew. Chem. Int. Ed., 6/2018, 57, 7200-7204
  • "A Synthetic Route to Sodium α-Aminoalkanesulfinates and Their Application in the Generation of α-Aminoalkyl Radicals for Radical Addition Reactions"
    Sakamoto, R.; Yoshii, T.; Takada, H.; *Maruoka, K.
    Org. Lett., 4/2018, 20, 2080-2083
  • "Catalyst-Controlled Diastereoselectivity Reversal in the Formation of Dihydropyrans"
    
*Kano, T.; Maruyama, H.; Homma, C.; *Maruoka, K.
    Chem. Commun., 4/2018, 54, 3496-3499
  • "Copper- Catalyzed C(sp) - C(sp3) Coupling of Terminal Alkynes with Alkylsilyl Peroxides via a Radical Mechanism"
    Sakamoto, R.; Kato, T.; Maruoka, K.
    Org. Lett. , 3/2018, 20(5), 1400-1403
  • "Alkylative Kinetic Resolution of Vicinal Diols under Phase- Transfer Conditions: A Chiral Ammonium Borinate Catalysis
"
    Pawliczek, M.; Hashimoto, T. Maruoka, K.
    Chem. Sci., 2/2018, 9(5), 1231-1235
  • "Chiral Amine-Catalyzed Asymmetric Conjugate Addition of Aldehydes to α-Phenylselenoenones as Formal Z-Allylating Agents"
    
Kano, T.; Maruyama, H.; Homma, C.; Maruoka, K.
    Chem. Commun. , 1/2018, 54(2), 176-179
  • "Asymmetric Synthesis of Less Accessible α-Tertiary Amines from Alkynyl Z-Ketimines"
    
Kano, T.; Aota, Y.; Maruoka, K.
    Angew. Chem. Int. Ed. , 12/2017, 56(51), 16293-16296
  • "Synthesis of Chiral Tritylpyrrolidine Derivatives and Their Application to Asymmetric Benzoyloxylation
"
    Shimogaki, M.; Maruyama, H.; Tsuji, S.; Homma, C.; Kano, T.; Maruoka, K.
    J. Org. Chem. , 12/2017, 82(23), 12928-12932
  • "The Direct C- H Difluoromethylation of Heteroarenes Based on the Photolysis of Hypervalent Iodine(III) Reagents That Contain Difluoroacetoxy Ligands"
    Sakamoto, R.; Kashiwagi, H.; Maruoka, K.
    Org. Lett. , 10/2017, 19(19), 5126-5129
  • "Hypervalent Iodine(III) Catalyzed Radical Hydroacylation of Chiral Alkylidenemalonates with Aliphatic Aldehydes under Photolysis
"
    Selvakumar, S.; Kang, Q.-K..; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; Maruoka, K.
    Tetrahedron, 10/2017, 73(40), 5841-5846
  • "Practical Synthesis of Two Different Pseudoenantiomeric Organocatalysts with cis-Cyclohexanediamine Structure from a Common Chiral Source
"
    Lee, H.-J.; Moteki, S. A.; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; Liu, Y.; Maruoka, K.
    Asian J. Org. Chem. , 9/2017, 6(9), 1226-1230
  • "Catalyst-Controlled, Enantioselective and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins"
    
Kan, S. B. J.; Maruyama, H.; Akakura, M.; Kano, T.; Maruoka, K.
    Angew. Chem. Int. Ed., 7/2017, 56(32), 9487-9491
  • "In- Situ Generation of N- Boc- Protected Alkenyl Imines: Controlling the E/Z Geometry of Alkenyl Moieties in the Mukaiyama- Mannich Reaction
"
    J.-F. Bai, J.-F.; Sasagawa, H.; Yurino, T.; Kano, T.; Maruoka, K.
    Chem. Commun. , 7/2017, 53(58), 8203-8206
  • "Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines"
    Sakamoto, R.; Sakurai, S.; Maruoka, K.
    Chem. Eur. J., 7/2017, 23(38), 9030-9033

Review

  • 「The Design of Environmentally-Benign, High-Performance Organocatalysts for Asymmetric Catalysis」 Sakamoto, R.; Maruoka, K. , J. Synth. Org. Chem., Jpn. , 75, 1141-1149, 11, 11/2017
  • 「Practical Synthesis of Both Enantiomeric Amino Acid, Mannich, and Aldol Derivatives by Asymmetric Organocatalysis
」 Liu, Y.; Arumugam, N.; Almansour, A. I.; Kumar, R. S.; Maruoka, K., Chem. Rec. , 17, 1059-1069, 10, 10/2017

Conference

  • 6th Japan-UK Symposium on Asymmetric Synthesis
    "Design of New, High-Performance Organoradical Catalysts with Privileged Structures for Asymmetric Catalysis", 招待講演
    Keiji Maruoka
    11/28/2018-11/29/2018, Fukuoka, Japan
  • The 13th International Symposium on Organic Reactions (ISOR-13)
    "Design of New, High-Performance Organoradical Catalysts with Privileged Structures for Asymmetric Catalysis", 招待講演
    Keiji Maruoka
    11/21/2018-11/24/2018, Hsinchu, Taiwan
  • The Organic Chemistry Day in Pavia
    "Asymmetric Enamine Catalysis with Nitroso and Related Compounds Catalyzed by High-Performance Organocatalysts", 招待講演
    Keiji Maruoka
    10/11/2018-10/11/2018, Pavia, Italy
  • Boehringer-Ingelheim Lectureship [2]
    "Design of Bifunctional Organocatalysts by Experimental and Computational Studies, and Design of New Organoradical Catalysts with Privileged Structure", 招待講演
    Keiji Maruoka
    8/11/2018-8/11/2018, Boston, U. S. A.
  • Boehringer-Ingelheim Lectureship [1]
    "Asymmetric Phase-Transfer Catalysis: Basic Design of Maruoka Catalyst® and the Industrial Application", 招待講演
    Keiji Maruoka
    8/10/2018-8/10/2018, Boston, U. S. A.
  • The Second Japanese-Spanish Symposium on Organic Synthesis
    "Advantage of Chiral Amino Organocatalysts over Proline in Asymmetric Enamine Catalysis: A Good Harmony with Water", 招待講演
    Keiji Maruoka
    5/28/2018-5/29/2018, Kyoto, Japan
  • Departmental Organic Seminar
    "Design of High-Performance Organocatalysts with Privileged Structures for Asymmetric Catalysis", 招待講演
    Maruoka, K.
    3/13/2018-3/13/2018, Alicante, Spain
  • 8th International Collaborative and Cooperative Chemistry Symposium (8th ICCCS)
    "Design of High-Performance Organocatalysts for Catalytic Asymmetric Synthesis", 招待講演
    Maruoka, K.
    12/18/2017-12/19/2017, Hyderabad, India
  • Singapore Japan Germany Trilateral Symposium on Precision Synthesis & Catalysis
    "Practical Synthesis of Four Different, Bifunctional Organocatalysts for Asymmetric Catalysis", 招待講演
    Maruoka, K.
    11/20/2017-11/21/2017, Singapore, Singapore
  • Second International Conference on Organic Chemistry at GDUT
    "Design of High-Performance Organocatalysts for Catalytic Asymmetric Synthesis ", 招待講演
    Maruoka, K.
    11/11/2017-11/12/2017, Guangzhou, China
  • 8th Pacific Symposium on Radical Chemistry
    "New Strategy of Generating Carbon Radicals for Organic Synthesis", 招待講演
    Maruoka, K.
    7/18/2017-7/22/2017, Brisbane, Australia
  • 4th Elemento-Organic Chemistry Symposium – Asymmetric Synthesis: The Methods and Applications
    "Design of High-Performance Organocatalysts with Privileged Structures for Asymmetric Catalysis", 招待講演
    Maruoka, K.
    7/14/2017-7/15/2017, Tianjin, China
  • 2nd International Conference on Hydrogen Atom Transfer (iCHAT 2017)
    "New Strategy of Generating Acyl Radicals for Organic Synthesis", 招待講演
    Maruoka, K.
    7/2/2017-7/6/2017, Rome, Italy

Domestic Conference

  • リトリートシンポジウム
    "高性能ハイブリッド触媒系を活用する高選択的ドミノ反応の開発", 口頭発表
    丸岡啓二
    1/31/2018-1/31/2018, 蒲郡
  • 第1回公開シンポジウム
    "高性能ハイブリッド触媒系を活用する高選択的ドミノ反応の開発", 口頭発表
    丸岡啓二
    1/30/2018-1/30/2018, 名古屋
  • 特別講演会
    "高性能有機触媒を活用する触媒的不斉合成の最前線", 招待講演
    丸岡啓二
    11/30/2017-11/30/2017, 岡山
  • キックオフシンポジウム
    "高性能ハイブリッド触媒系を活用する高選択的ドミノ反応の開発", 口頭発表
    丸岡啓二
    9/14/2017-9/14/2017, 東京

Media

  • Synfacts
    「Indanol-Based Chiral Organoiodine Catalysts for Enantioselective Hydrative Dearomatization」
    Hashimoto, T.; Shimazaki, Y.; Omatsu, Y.; *Maruoka, K. , 4/2018