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  • 京都大学 大学院理学研究科 化学専攻 有機合成化学研究室
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研究実績

2017
Asymmetric Synthesis of Less Accessible α-Tertiary Amines from Alkynyl Z-Ketimines
T. Kano, Y. Aota, K. Maruoka, Angew. Chem. Int. Ed., in print.

Synthesis of Chiral Tritylpyrrolidine Derivatives and Their Application to Asymmetric Benzoyloxylation
M. Shimogaki, H. Maruyama, S. Tsuji, C. Homma, T. Kano, K. Maruoka, J. Org. Chem., in print.

The Direct C-​H Difluoromethylation of Heteroarenes Based on the Photolysis of Hypervalent Iodine(III) Reagents That Contain Difluoroacetoxy Ligands
R. Sakamoto, H. Kashiwagi, K. Maruoka, Org. Lett., 19, 5126-5129 (2017).

Hypervalent Iodine(III) Catalyzed Radical Hydroacylation of Chiral Alkylidenemalonates with Aliphatic Aldehydes under Photolysis
S. Selvakumar, Q.-K. Kang, N. Arumugam, A. I. Almansour, R. S. Kumar, K. Maruoka, Tetrahedron, 73, 5841-5846 (2017).

Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes
Y. Liu, D. Huang, J. Huang, K. Maruoka, J. Org. Chem., in print.

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, H. Sasagawa, T. Yurino, T. Kano, K. Maruoka, Chem. Commun., 53, 8203-8206 (2017).

Catalyst-Controlled, Enantioselective and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins

S. B. J. Kan, H. Maruyama, M. Akakura, T. Kano, K. Maruoka, Angew. Chem. Int. Ed., 56, 9487-9491 (2017). (Highlighted in SYNFACTS, 2017, 985)

Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines
R. Sakamoto, S. Sakurai, K. Maruoka, Chem. Eur. J., 23, 9030-9033 (2017).

Practical Synthesis of Two Different Pseudoenantiomeric Organocatalysts with cis-Cyclohexanediamine Structure from a Common Chiral Source
H.-J. Lee, S. A. Moteki, N. Arumugam, A. I. Almansour, R. S. Kumar, Y. Liu, K. Maruoka, Asian J. Org. Chem., 6, 1226-1230 (2017).

Bis(trialkylsilyl) Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides
R. Sakamoto, S. Sakurai, K. Maruoka, Chem. Commun., 53, 6484-6487 (2017).

In situ Generation of less Accessible Boc-Imines from Aldehydes: Construction of a Quaternary Carbon by the Mannich Reaction or Unprecedented Aldol Reaction
T. Kano, C. Homma, K. Maruoka, Org. Biomol. Chem., 15, 4527-4530 (2017). (Highlighted in SYNFACTS2017, 873)

Practical Synthesis of Both Enantiomeric Amino Acid, Mannich, and Aldol Derivatives by Asymmetric Organocatalysis
Y. Liu, N. Arumugam, A. I. Almansour, R. S. Kumar, K. Maruoka, Chem. Rec., 17, 1059-1069 (2017).

Phase-Transfer Catalyzed Asymmetric Synthesis of α,β-Unsaturated γ,γ-Disubstituted γ-Lactams
A. Arlt, H. Toyama, K. Takada, T. Hashimoto, K. Maruoka, Chem. Commun., 53, 4779-4782 (2017).

Chiral Tertiary Sulfonium Salts as Effective Catalysts for Asymmetric Base-Free
Neutral Phase-Transfer Reactions
S. Liu, K. Maruoka, S. Shirakawa, Angew. Chem. Int. Ed., 56, 4819-4823 (2017).

A New Strategy for Organocatalyzed Asymmetric Synthesis of BINOL Derivatives
S. Shirakawa, K. Maruoka, Chem, 2, 329-331 (2017).

Hydrogen-Bonding Catalysis of Sulfonium Salts
S. Kaneko, Y. Kumatabara, S. Shimizu, K. Maruoka, S. Shirakawa, Chem. Commun., 53, 119-122 (2017).

Synthesis of the Right-Side Structure of Type B Physalins
M. Morita, S. Kojima, M. Ohkubo, H. Koshino, D. Hashizume, G. Hirai, K. Maruoka, M. Sodeoka, Isr. J. Chem., 57, 309-318 (2017).



2016
[2+2] Photocycloadditions between the Carbon-Nitrogen Double Bonds of Imines and Carbon-Carbon Double Bonds
R. Sakamoto, T. Inada, S. Sakurai, K. Maruoka, Org. Lett., 18, 6252-6255 (2016). (Highlighted in SYNFACTS2017, 240)

Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer
T. Kano, Y. Aota, K. Maruoka, Adv. Synth. Catal.358, 2996-2999 (2016).

Design of Bifunctional Quaternary Phosphonium Salt Catalysts for CO2 Fixation Reaction with Epoxides under Mild Conditions
S. Liu, N. Suematsu, K. Maruoka, S. Shirakawa, Green Chem., 18, 4611-4615 (2016).

Hydrogen-Bonding Catalysis of Tetraalkylammonium Salts in an Aza-Diels-Alder Reaction
Y. Kumatabara, S. Kaneko, S. Nakata, S. Shirakawa, K. Maruoka, Chem. Asian J., 11, 2126-2129 (2016).

Efficient Generation of Perfluoroalkyl Radicals from Sodium Perfluoroalkanesulfinates and a Hypervalent Iodine(III) Reagent: Mild, Metal-free Synthesis of Perfluoroalkylated Organic Molecules 
R. Sakamoto, H. Kashiwagi, S. Selvakumar, S. A. Moteki, K. Maruoka, Org. Biomol. Chem.14, 6417-6421 (2016).

A Bulky Thiyl-Radical Catalyst for the [3+2] Cyclization of N-Tosyl Vinylaziridines and Alkenes
T. Hashimoto, K. Takino, K. Hato, K. Maruoka, Angew. Chem. Int. Ed., 55, 8081-8085 (2016).

N-Boc-Aminals as Easily Accessible Precursors for Less Accessible N-Boc-Imines: Facile Synthesis of Optically Active Propargylamine Derivatives Using Mannich-Type Reactions 
T. Yurino, Y. Aota, D. Asakawa, T. Kano, K. Maruoka, Tetrahedron72, 3687-3700 (2016).

A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization
Y. Kawamata, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc., 138, 5206-5209 (2016).

Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents
S. Selvakumar, R. Sakamoto, K. Maruoka, Chem. Eur. J.22, 6552-6555 (2016).

Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines
T. Kano, R. Kobayashi, K. Maruoka, Org. Lett., 18, 276-279 (2016). (Highlighted in SYNFACTS2016, 292)

Efficient Photolytic C–H Bond Functionalization of Alkylbenzene with Hypervalent Iodine(III) Reagent
R. Sakamoto, T. Inada, S. Selvakumar, S. A. Moteki, K. Maruoka, Chem. Commun., 52, 3758-3761 (2016).

Catalytic Asymmetric Synthesis of Axially Chiral 2-Amino-1,10-Biaryl Compounds by Phase-Transfer-Catalyzed Kinetic Resolution and Desymmetrization
S. Shirakawa, X. Wu, S. Liu, K. Maruoka, Tetrahedron72, 5163-5171 (2016).



2015
Boronic Acid-Catalyzed, Highly Enantioselective Aza-Michael Additions of Hydroxamic Acid to Quinone Imine Ketals.
T. Hashimoto, A. O. Galvez, K. Maruoka,  J. Am. Chem. Soc., 137, 16016-16019 (2015).

Tetraalkylammonium Salts as Hydrogen-Bonding Catalysts.
S. Shirakawa, S. Liu, S. Kaneko, Y. Kumatabara, A. Fukuda, Y. Omagari, K. Maruoka, Angew. Chem. Int. Ed.54, 15767-15770 (2015).

Brønsted Acid-Catalyzed Mannich Reaction through Dual Activation of Aldehydes and N-Boc-imines.
T. Kano, Y. Aota, D. Asakawa, K. Maruoka, Chem. Commun., 51, 16472-16474 (2015). (Cover Picture)

Mechanism of Metal-Free C-H Activation of Branched Aldehydes and Acylation of Alkenes Using Hypervalent Iodine Compound: A Theoretical Study. 
J. Jiang, R. Ramozzi, S. A. Moteki, A. Usui, K. Maruoka, K. Morokuma, J. Org. Chem., 80, 9264-9271 (2015).

Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine. 
T. Kano, H. Sugimoto, H. Maruyama, K. Maruoka, Angew. Chem. Int. Ed., 54, 8462-8465 (2015). (Highlighted in SYNFACTS2015, 986)

Versatile In Situ Generated N-Boc-Imines: Application to Phase-Transfer-Catalyzed Asymmetric Mannich-Type Reactions. 
T. Kano, R. Kobayashi, K. Maruoka, Angew. Chem. Int. Ed., 54, 8471-8474 (2015). (Highlighted in SYNFACTS2015, 987)

Regioselectivity Switch in Chiral Amine-Catalyzed Asymmetric Addition of Aldehydes to Reactive Enals. 
T. Kano, H. Maruyama, R. Sakamoto, K. Maruoka, Chem. Commun., 51, 10062-10065 (2015).

Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions. 
T. Hashimoto, K. Maruoka, Chem. Rev., 115, 5366-5412 (2015).

Positive Effect of Water in Asymmetric Direct Aldol Reactions with Primary Amine Organocatalyst: Experimental and Computational Studies. 
S. A. Moteki, H. Maruyama, K. Nakayama, H.-B. Li, G. Petrova, S. Maeda, K. Morokuma, K. Maruoka, Chem. Asian J., 10, 2112-2116 (2015).

Catalytic Asymmetric Diels-Alder Reaction of Quinone Imine Ketals: A Site-Divergent Approach. 
T. Hashimoto, H. Nakatsu, K. Maruoka, Angew. Chem. Int. Ed., 54, 4617-4621 (2015).

Phase-Transfer-Catalyzed Asymmetric Desymmetrizations of Cyclopentanones. 
S. Shirakawa, T. Tokuda, S. B. J. Kan, K. Maruoka, Org. Chem. Front., 2, 336-339 (2015).

Phase-Transfer-Catalyzed Asymmetric SNAr Reaction of α-Amino Acid Derivatives with Arene Chromium Complexes.
S. Shirakawa, K. Yamamoto, K. Maruoka, Angew. Chem. Int. Ed., 54, 838-840 (2015).



2014
A Practical Approach for the Oxidation of Unactivated Csp3-H Bonds with o-Nitro(Diacetoxyiodo)Benzene as an Efficient Hypervalent Iodine(III)-Based Oxidizing Agent.   
S. A. Moteki, S. Sermadurai, T. Zhang, A. Usui, K. Maruoka, Asian J. Org. Chem., 3, 932 (2014). (Cover Picture)

Metal-Free C-H Bond Activation of Branched Aldehydes with Hypervalent Iodine(III) Catalyst under Visible-Light Photolysis: Successful Trapping with Electron-Deficient Olefins.
S. A. Moteki, A. Usui, S. Sermadurai, T. Zhang, K. Maruoka, Angew. Chem. Int. Ed., 53,11060 (2014). (Very Important Papers)

An Organic Thiyl Radical Catalyst for Enantioselective Cyclization.
T. Hashimoto, Y. Kawamata, K. Maruoka, Nat. Chem., 6, 702 (2014).

Efficient Asymmetric Synthesis of Spiro-2(3H)-Furanones via Phase-Transfer-Catalyzed Alkynylation.
X. Wu, S. Shirakawa, K. Maruoka, Org. Biomol. Chem., 12, 5388 (2014).

Effect of Bronsted Acid Co-Catalyst in Asymmetric Conjugate Addition of 3-Aryloxindoles to Maleimide under Base-Free Phase-Transfer Conditions. 
S. Shirakawa, H. Makino, T. Yoshidome, K. Maruoka, Tetrahedron70, 7128 (2014).

Design and Synthesis of a Biphenyl-based Chiral Amino Sulfonamide with High Catalytic Performance in Mannich Reactions.
T. Kano, H. Maruyama, K. Akiyama, K. Maruoka, Tetrahedron Lett., 55, 4227 (2014).

Asymmetric Phase-Transfer Reactions under Base-Free Neutral Conditions.
S. Shirakawa, K. Maruoka, Tetrahedron Lett., 55, 3833 (2014).

Catalytic Asymmetric Synthesis of 3,3'-Diaryloxindoles as Triarylmethanes with a Chiral All-Carbon Quaternary Center: Phase-Transfer-Catalyzed SNAr Reaction.
S. Shirakawa, K. Koga, T. Tokuda, K. Yamamoto, K. Maruoka, Angew. Chem. Int. Ed., 53,6220 (2014).

Catalytic Asymmetric Alkylation of 3-Aryl-Substituted Oxindoles to give 3,3-Disubstituted Oxindoles under Phase-Transfer Conditions.
F. Deng, S. A. Moteki, K. Maruoka, Asian J. Org. Chem., 3, 395 (2014).

Phase-Transfer-Catalyzed Asymmetric α-Arylation of α-Amino Acid Derivatives.
S. Shirakawa, K. Yamamoto, T. Tokuda, K. Maruoka, Asian J. Org. Chem., 3, 433 (2014).

A Metal-Free Golden Age.
K. Maruoka, Asian J. Org. Chem., 3, 319 (2014).

A Base-Free Neutral Phase-Transfer Reaction System.
S. Shirakawa, L. Wang, R. He, S. Arimitsu, K. Maruoka, Chem. Asian J., 9, 1586 (2014).

Asymmetric Phase-Transfer Catalysis with Homo- and Heterochiral Quaternary Ammonium Salts: A Theoretical Study.
G. P. Petrova, H.-B. Li, K. Maruoka, K. Morokuma, J. Phys. Chem. B118, 5154 (2014).

Synthesis of 3-Mono-Substituted Binaphthyl-Based Secondary Amine Catalysts via Monobromination of an Axially Chiral Dicarboxylic Acid Derivative.
T. Kano, M. Takeda, R. Sakamoto, K. Maruoka, J. Org. Chem., 79, 4240 (2014).

Catalytic Enantioselective Intramolecular Cyclization of N-aryl Diazoamides Using a Titanium-BINOLate Complex.
T. Hashimoto, K. Yamamoto, K. Maruoka, Chem. Commun. (Cambridge) 50, 3220 (2014).

Practical Approach for Asymmetric Hydroxyamination of Aldehydes with in Situ Generated Nitrosocarbonyl Compounds: Application to One-Pot Synthesis of Chiral Allylamines.
T. Kano, F. Shirozu, K. Maruoka, Org. Lett., 16, 1530 (2014).

Amine-Catalyzed Asymmetric Cross-Aldol Reactions Using Heterofunctionalized Acetaldehydes as Nucleophiles.
T. Kano, R. Sakamoto, K. Maruoka, Org. Lett., 16, 944-947 (2014).

Chiral Brønsted Acid-catalyzed Enantioselective Addition of Indoles to Ketimines.
T. Kano, R. Takechi, R. Kobayashi, K. Maruoka, Org. Biomol. Chem., 12, 724-727 (2014). (Most Downloaded Articles)(Cover Picture)

Remote Chirality Control Based on the Organocatalytic Asymmetric Mannich Reaction of α-Thio Acetaldehydes.
T. Kano, R. Sakamoto, K. Maruoka, Chem. Commun., 50, 942-944 (2014). (Most Downloaded Articles)