Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kumamoto University
Kumamoto University Graduate School of Life Sciences Molecular Medicinal Chemistry Laboratory
Research achievements
Publication
2024
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Mechanistic Investigations of Chiral Lithium Binaphtholate Catalysis for Asymmetric Aldol-Tishchenko Reaction of α-Fluoroarylketones
Kotani, S.; Asano, T.; Arae, S.; Sugiura, M. Nakajima, M.
J. Org. Chem. In press.
2023
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Lithium binaphtholate-catalyzed asymmetric Michael reaction of acrylamides
Harada, N.; Asano, T.; Sugiura, M.; Kotani, S.; Nakajima, M.
Chem Pharm. Bull. 2023, 71, 792–797. -
Enantioselective and Chemoselective Phosphine Oxide-catalyzed Aldol Reaction of N-Unprotected Cyclic Carboxyimides
Yoshiwara, Y.; Kotani, S.; Nakajima, M.
Chem. Eur. J. 2023, e202203506.
Catalysis with Earth-abundant Elements; CHAPTER 11: Catalysis by Silicon Species
Sugiura, M .; Kotani, S .; Nakajima, M.
RSC Catalysis Series 2021-January (40) 309-333 2021CHIRAL PHOSPHINE OXIDE-CATALYZED ENANTIOSELECTIVE RING OPENING OF OXETANES
Kotani, S .; Tashima, Y .; Tanaka, H .; Aoki, S .; Nakajima M. 2021 , 103 , 1048–1056,
Heterocycles, In press.
2022
2021
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Catalysis with Earth-abundant Elements; CHAPTER 11: Catalysis by Silicon Species
Sugiura, M.;Kotani, S.; Nakajima, M.
RSC Catalysis Series 2021, 40, 309-333. -
CHIRAL PHOSPHINE OXIDE-CATALYZED ENANTIOSELECTIVE RING OPENING OF OXETANES
Kotani, S.; Tashima, Y.; Tanaka, H.; Aoki, S.; Nakajima M. 2021, 103, 1048–1056,
Heterocycles, 2021, 103, 1048–1056. -
Molecular recognition of a single-chain Fv antibody specific for GA-pyridine, an advanced glycation end-product (AGE), elucidated using biophysical techniques and synthetic antigen analogues.
Kobashigawa, Y.; Ohara, T.; Morita, K.; Toyota, Y.; Nakamura, T.; Kotani, S.; Arimori, T.; Yamauchi, S.; Liu, C.; Kitazaki, M.; Wakayama- Miyazaki, Y.; Suwa, Y.; Uchida-Kamekura, M.; Fukuda, N.; Sato, T.; Nakajima, M.; Takagi, J. Yamagata, Y.; Morioka, H.
J. Biochem., 2021, 170, 379–387.
2020
Synthesis of conjugated multiunsaturated thioesters via one-pot TiCl4-promoted aldol condensation.
Boateng, A .; Harada, T .; Ashikari, Y .; Nakajima, M .; Sugiura, M.
Tetrahedron Lett. 2020 , 61 , 152280.Phosphine-oxide-catalyzed Enantioselective Cross-aldol Reaction of Aldehydes with Trichlorosilane as Lewis Acid Promoter.
Kotani, S .; Hanamure, T .; Mori, Y .; Nakajima, M. ChemCat Chem 2020, 12, 4780–4783 ..O -Monoacyltartaric Acid / (Thio) urea Cooperative Organocatalysis for Enantioselective Conjugate Addition of Boronic Acid.
Yoshimitsu, T. Kuboyama, Y. Nishiguchi, S. Nakajima, M. Sugiura, M. Org. Lett. 2020 , 22 , 3780-3784.Recent Advances in Asymmetric Phosphine Oxide Catalysis.
Kotani, S .; Nakajima, M. Tetrahedron Lett . 2020 , 61, 151421.
2019
Lewis Base-catalyzed Enantioselective Conjugate Reductions of β, β-Disubstituted α, β-Unsaturated Ketones with Trichlorosilane: E / Z Isomerization, Regioselectivity, and Synthetic Applications.
Sugiura, M .; Ashikari, Y .; Takahashi, Y .; Yamaguchi, K .; Kotani, S .; Nakajima, M. J. Org. Chem. 2019, 84, 11458-11473.
Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts.
Hashimoto, Y .; Michimuko, C .; Yamaguchi, K .; Nakajima, M .; Sugiura, M. J. Org. Chem. 2019, 84, 9313-9321.
Stereoselective Synthesis of 2-Fluoro-1,3-diols via Lithium Binaphtholate-catalyzed Aldol-Tishchenko Reaction.
Asano, T .; Kotani, S .; Nakajima, M. Org. Lett 2019, 21, 4192-4196.
Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Shimoda, Y .; Nakajima, M. Chem. Pharm. Bull. 2019, 67, 452-446.
2018
Catalytic Enantioselective Aldol Reactions of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis.
Kotani, S .; Yoshiwara, Y .; Ogasawara, M .; Sugiura, M .; Nakajima, M. Angew. Chem. Int. Ed. 2018, 57, 15877-15881.
Dramatic Enantioselectivity Reversal in the Propargylation of Aldehyde with Alkynyllithium Catalyzed by Dilithium Binaphtholate Derivatives.
Nakajima, M .; Watanabe, R .; Osakama, K .; Sakamoto, M .; Takemoto, D. Kukita, K. Heterocycles 2018, 97, 708-711
2017
Development of asymmetric aldol reaction using phosphine oxide as an organomolecular catalyst.
Makoto Nakajima, Chemical industry 2017, 68, 66-72.
Stereoselective Synthesis of Nitrogen-containing Compounds from Enamines.
Sugiura, M .; Kashiwagi, T .; Ito, M .; Kotani, S .; Nakajima, M. J. Org. Chem. 2017, 82, 10968-10979.
Asymmetric Aldol / Vinylogous Aldol / Cyclization Reaction Using Phosphine Oxide Catalysts.
Alim, NR; Miyazaki, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Kotani, S. Chem. Pharm. Bull. 2017, 65, 989-993.
Chiral Lithium Binaphtholate for Enantioselective Amination of Acyclic α-Alkyl-β-keto Esters: Application to the Total Synthesis of L-Carbidopa.
Asano, T .; Moritani, M .; Nakajima. M .; Kotani, S. Tetrahedron 2017, 73, 5975-5982.
Sequential Catalysis of Phosphine Oxide for Stereoselective Synthesis of Stereopentads.
Kotani, S .; Kai, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2017, 19, 3672-3675.
Enantioselective Chlorinative Aldol Reaction of α-Substituted Acroleins Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Hanamure, T .; Nozaki, H .; Sugiura, M .; Nakajima, M. Tetrahedron Asymmetry 2017, 28, 282-287.
2016
Enantioselective Michael Addition of a Malonate Ester to a Maleate Ester Catalyzed by Lithium Binaphtholate.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Nakajima, M. Synlett 2016, 27, 2477-2780.
Enantioselective Amination of Acyclic α-Alkylated β-Keto Esters Catalyzed by Chiral Lithium Binaphtholate.
Kotani, S .; Asano, T .; Moritani, M .; Nakajima, M. Tetrahedron Lett. 2016, 57, 4217-4219.
Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones.
Osakama, K .; Nakajima, M. Org. Lett. 2016, 18, 236-239.
Stereoselective Synthesis of Highly Functionalized 2,3-Dihydro-4-pyranones Using Phosphine Oxide as Catalyst.
Kotani, S .; Miyazaki, S .; Kawahara, K .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Chem. Pharm. Bull. 2016, 64, 189-192.
Concise Asymmetric Construction of C2-Symmetric 1,9-Diarylnonanoids Using Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone.
Kotani, S., Kai, K., Shimoda, Y., Hu, H., Gao, S., Sugiura, M., Ogasawara, M. & Nakajima, M.Chem. Asian J.2016, 11, 376-379.
Indoxyl Sulfate Potentiates Skeletal Muscle Atrophy by Inducing the Oxidative Stress-mediated Expression of Myostatin and Atrogin-1.
Enoki, Y .; Watanabe H .; Arake, R .; Sugimoto, R .; Imafuku, T .; Tominaga, Y .; Ishima, Y .; Kotani, S .; Nakajima, M .; Tanaka, M .; Matsushita , K .; Fukagawa, M .; Otagiri, M .; Maruyama, T. Sci. Rep. 2016, 6, 32084.
2015
Tertiary Amine as a Nucleophile Carrier: α-Aminonitrile in the Cyanation of Acetals and Orthoesters.
Kotani, S .; Sakamoto, M .; Osakama, K .; Nakajima, M. Eur. J. Org. Chem. 2015, 30, 6606-6609.
One-pot Synthesis of β, β-Disubstituted α, β-Unsaturated Carbonyl Compounds using Sequential Ti-Aldol Addition to Ketones and Elimination.
Sugiura, M .; Ashigari, Y .; Nakajima, M. J. Org. Chem. 2015, 80, 8830-8835.
Nitration of Indoxyl Sulfate Facilitates Its Cytotoxicity in Human Renal Proximal Tubular Cells via Expression of Heme Oxygenase-1.
Ishima, Y .; Narisoko, T .; Kragh-Hansen, U .; Kotani, S .; Nakajima, M .; Otagiri, M .; Maruyama, T. Biochemi. Biophys. Res. Commun. 2015, 465, 481-487
Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acid.
Sugiura, M .; Ishikawa, W .; Kuboyama, Y .; Nakajima, M. Synthesis 2015, 47, 2265-2269.
Chiral Lithium Binaphtholate for Enantioselective Michael Addition of Acyclic α-Alkyl-β-keto Esters to Vinyl Ketones.
Kotani, S .; Moritani, M .; Nakajima, M. Asian J. Org. Chem. 2015, 4, 616-618.
-2014
Phosphine Oxide-Catalyzed Enantioselective Intramolecular Aldol Reaction via Regioselective Enolization of Unsymmetrical Diketones with Tetrachlorosilane.
Kotani, S .; Aoki, S .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Org. Lett. 2014, 16, 4802-4805.O-Monoacyltartaric Acid-Catalyzed Enantioselective Conjugate Addition of a Boronic Acid to Dienones: Application to the Synthesis of Optically Active Cyclopentenones.
Sugiura, M .; Kinoshita, R .; Nakajima, M. Org. Lett. 2014, 16, 5172-5175.Human Organic Anion Transporters Function as a High-capacity Transporter for p-Cresyl Sulfate, a Uremic Toxin.
Watanabe, H .; Sakaguchi, Y .; Sugimoto, R .; Kaneko, K .; Iwata, H .; Kotani, S .; Nakajima, M .; Ishima, Y .; Otagiri, M .; Maruyama, T. Clinical and Experimental Nephrology 2014, 18, 814-820.Imino Ene-type Reaction of Enamines with N-Sulfonylimines and Application to Diastereoselective Synthesis of 1,3-Diamines.
Itoh, M .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 4082-4085.Lithium Binaphtholate-catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds.
Kotani, S .; Kukita, K .; Tanaka, K .; Ichibakase, T .; Nakajima, M. J. Org. Chem. 2014, 79, 4809-4816.Diastereoselective Synthesis of 1,3-Diamines by a Domino Reaction of Imines, Enamines, and Trichlorosilane.
Kashiwagi, T .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 1924-1926.Enantioselective Double Aldol Reactions Involving the Sequential Activation of Silicon Tetrachloride by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima, M. Synlett 2014, 25, 631-640.Skeleton construction utilizing continuous aldol reaction-Development to stereoselective polyol synthesis-.
Shunsuke Kotani, Masaharu Sugiura, Makoto Nakajima Chemistry 2013, 68, 64-65.Atropisomeric Chiral Diene in Asymmetric Catalysis: C2-Symmetric (Z, Z) -2, 3-Bis [1- (diphenylphosphinyl) ethylidene] tetralin as Highly Active Lewis Base Organocatalyst.
Ogasawara, M .; Kotani, S .; Nakajima, H .; Furusho, H .; Miyasaka, M .; Shimoda, Y .; Wu, W.-Y .; Sugiura, M .; Takahashi, T .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 13798-13802.Enantioselective Morita–Baylis–Hillman Reaction Catalyzed by a Chiral Phosphine oxide.
Kotani, S .; Itoh, M .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Tetrahedron Lett. 2013, 54, 6430-6433.Enantioselective Aldol Reaction Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima. Chem. Rec. 2013, 13, 362-370.Stereoselective Synthesis of Multiple Stereocenters by Using a Double Aldol Reaction.
Shimoda, Y .; Kubo, T .; Sugiura, M .; Kotani, S .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 3461-3464.Facile Synthesis of Chiral 1,2-Chlorohydrins via the Ring-opening of meso-Epoxides Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Furusho, H .; Tokuoka, E. Nakajima, M. Tetrahedron 2013, 69, 3075-3081.Enantioselective Aldol Reactions Catalyzed by Chiral Lewis Bases.
Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 4, pp 198-209.Allylations of C–O and C–N Double Bonds and Related Reactions.
Sugiura, M .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 214-233.C–X Bond Formation: Organocatalytic Enantioselective Halogenation of meso Epoxides.
Kotani, S .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 506-517.Interaction between Two Sulfate-Conjugated Uremic Toxins, p-Cresyl Sulfate and Indoxyl Sulfate, during Binding with Human Serum Albumin.
Watanabe, H .; Noguchi, T .; Miyamoto, Y .; Kadowaki. D .; Kotani, S .; Nakajima, M .; Miyamura, S .; Ishima, Y .; Otagiri, M .; Maruyama, T. Drug Metab. Dispos. 2012, 40, 1423-1428.Efficient Preparation of 1,3-Diol derivatives with Three Contiguous Stereocenters by an Enantioselective Direct Aldol-Tishchenko Reaction.
Ichibakase, T .; Nakajima, M. Synthesis 2012, 44, 3145-3151.Enantioselective Reductive Aldol Reaction using Teriary Amine as Hydride Donor
Kotani, S .; Osakama, K .: Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2012, 53, 4199-4201.Synthesis of Aryl Group-modified DIOP Dioxides (Ar-DIOPOs) and Their Application as Modular Lewis Base Catalysts.
Ohmaru, Y .; Sato, N .; Mizutani, M .; Kotani, S .; Sugiura, M .; Nakajima, M. Org. Biomol. Chem. 2012, 10, 4562-4570.Trichlorosilyl Triflate Mediated-Enantioselective Directed Cross-Aldol Reaction between Ketones using Chiral Phosphine Oxide as an Organocatalyst.
Aoki, S .; Kotani, S .: Sugiura, M .; Nakajima, M. Chem. Commun. 2012, 48, 5524-5526.Construction of Quaternary Carbon Centers by Base-catalyzed Enantioselective Aldol Reaction and Related Reaction of Trimethoxysilyl Enol Ethers.
Ichibakase, T .; Kaneko, T .; Orito, Y .; Kotani, S .; Nakajima, M. Tetrahedron 2012, 68, 4210-4224.Organic Anion Transporters Play an Important Role in the Uptake of p-Cresyl Sulfate, a Uremic Toxin, in the Kidney.
Miyamoto, Y .; Watanabe, H .; Noguchi, T .; Kotani, S .; Nakajima, M .; Kadowaki, D .; Otagiri, M .; Maruyama, T. Nephrology Dialysis Transplantation 2011, 26, 2498-2502.A Tertiary Amine as A Hydride Donor: Trichlorosilyl Triflate-mediated Conjugate Reduction of Unsaturated Ketones.
Kotani, S .; Osakama, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2011, 13, 3968-3971.Enantioselective Evans-Tishchenko Reduction of β-Hydroxyketone Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Nakatsu, M .; Nakajima, M. Molecules 2011, 52, 5008-5019.Enantioselective Double Aldol Reaction Catalyzed by Chiral Phosphine Oxide.
Shimoda, Y .; Kotani, S .; Sugiura, M .; Nakajima, M. Chem. Eur. J. 2011, 17, 7992-7995.Trichlorosilyl Triflate for Enantioselective Direct-type Aldol Reaction with Chiral Phosphine Oxide.
Kotani, S .; Aoki, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2011, 52, 2834-2836.Lithium Acetylides as Alkynylating Reagents for the Enantioselective Alkynylation of Ketones Catalyzed by Lithium Binaphtholate.
Tanaka, K .; Kukita, K .; Ichibakase, T .; Kotani, S .; Nakajima, M. Chem Commun. 2011, 47, 5614-5616.Direct Enantioselective Aldol-Tishchenko Reaction Catalyzed by Chiral Lithium Diphenylbinaphtholate.
Ichibakase, T .; Nakajima, M. Org. Lett. 2011, 13, 1579-1581.Synthesis of γ-Amino Alcohols from Aldehydes, Enamines, and Trichlorosilane using Lewis Base Catalysts.
Kashiwagi, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2011, 67, 531-539.Enantioselective Conjugate Addition of Boronic Acids to Enones Catalyzed by O-Monoacyltartaric Acids.
Sugiura, M .; Tokudomi, M .; Nakajima, M.Chem. Commun. 2010, 46, 7799-7800.Enantioselective Alkynylation of Carbonyl Compounds with Trimethoxysilylalkynes Catalyzed by Lithium Binaphtholate.
Ueda, T .; Tanaka, K .; Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron 2010, 66, 7726-7731.“Roofed” β-Iminodisulfides as New Chiral Ligands for Palladium-Catalyzed, Asymmetric Allylic Alkylation.
Matsunaga, H .; Tokuda, R .; Nakajima, M .; Ishizuka, T. Chem. Pharm. Bull. 2010, 58, 1419-1421.Development of a direct asymmetric aldol reaction catalyzed by an organic oxide compound.
Makoto Nakajima, Chemical Industry, 2010, 61, 662-666.Development of Chiral Dinitrones as Modular Lewis Base Catalysts: Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes.
Oh, YS; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry 2010, 21, 1833-1835.DMAP-catalyzed Cyanation of Aldehydes and Ketones with Ethyl Cyanoformate.
Aoki, S .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2010, 51, 3547-3549.Enantioselective Alkynylation of Ketones with Trimethoxysilylalkynes using Lithium Binaphtholate as a Catalyst.
Tanaka, K .; Ueda, T .; Ichibakase, T .; Nakajima, M. Tetrahedron Lett. 2010, 51, 2168-2169.Diastereo- and Enantioselective Reductive Aldol Reaction with Trichlorosilane Using Chiral Lewis Bases as Organocatalysts.
Sugiura, M .; Sato, N .; Sonoda, Y .; Kotani, S .; Nakajima .; M. Chem. Asian J. 2010, 5, 478-481.Aldol reaction to build quaternary asymmetric carbon.
Makoto Nakajima, pp 248-249 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Enone's asymmetric reducing aldol reaction.
Masaharu Sugiura, Makoto Nakajima, pp 472-473 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Novel Enantioselective Direct Aldol-type Reaction Promoted by Chiral Phosphine Oxide as an Organocatalyst.
Kotani, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2009, 50, 4602-4605.Enantioselective Aldol Reaction of Silyl Ketene Acetals Promoted by a Lewis Base-activated Lewis Acid Catalyst.
Shimoda, Y .; Tando, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry, 2009, 20, 1369-1370.Asymmetric Synthesis of 4H-1,3-Oxazines: Enantioselective Reductive Cyclization of β-Amino Enones with Trichlorosilane Catalyzed by Chiral Lewis Bases.
Sugiura, M .; Kumahara, M .; Nakajima, M. Chem. Commun. 2009, 3585-3587.Base-catalyzed asymmetric synthesis reaction that activates chlorosilyl compounds.
Makoto Nakajima, pp131-136 "Frontier 21 Evolving Organic Catalyst" Supervised by Keiji Maruoka, Kagaku-Dojin, 2009.A Chiral "Roofed" cis-Diamine-Ru (II) Complex: An Efficient Catalyst for Asymmetric Transfer Hydrogenation of Ketimines.
Matsunaga, H .; Nakanishi, K .; Nakajima, M .; Kunieda, T .; Ishizuka, T. Heterocycles, 2009, 78, 617-622.Lewis Base-catalyzed Conjugate Reduction and Reductive Aldol Reaction of α, β-Unsaturated Ketones Using Trichlorosilane.
Sugiura, M .; Sato, N .; Kotani, S .; Nakajima, M. Chem. Commun. 2008, 4309-4311.Enantioselective Construction of Quaternary Asymmetric Carbon Centers Using an Aldol Reaction of Trimethoxysilyl Enol Ethers Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron Lett. 2008, 49, 4427-4429.First Asymmetric Abramov-type Phosphonylation of Aldehydes with Trialkyl Phosphites Catalyzed by Chiral Lewis Bases.
Nakanishi, K .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2008, 64, 6415-6419.Chiral Phosphine Oxide BINAPO as a Lewis Base Catalyst for Asymmetric Allylation and Aldol Reaction of Trichlorosilyl Compounds.
Kotani, S .; Hashimoto, S .; Nakajima, M. Tetrahedron 2007, 63, 3122-3132.Catalytic Enantioselective Tandem Carbonyl Ylide Formation / 1,3-Dipolar Cycloaddition Reactions of α-Diazo Ketones with Aromatic Aldehydes using Dirhodium (II) Tetrakis [N-benzene-fused-phthaloyl- (S) -valinate].
Tsutsui, H .; Shimada, N .; Abe, T .; Anada, M .; Nakajima, M .; Nakamura, S .; Nambu, H .; Hashimoto, S. Adv. Synth. Catal. 2007, 349, 521-526.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by the Chiral Phosphine Oxide BINAPO.
Kotani, S .; Hashimoto, S .; Nakajima, M. Synlett 2006, 1116-1118.Lewis Base Catalyzed Asymmetric Reactions Involving Hypervalent Silicate Intermediates.
Orito, Y .; Nakajima, M. Synthesis 2006, 1391-1401.Chiral Base-Catalyzed Aldol Reaction of Trimethoxysilyl Enol Ethers: Effect of Water as an Additive on Stereoselectivities.
Orito, Y .; Hashimoto, S .; Ishizuka, T .; Nakajima, M. Tetrahedron 2006, 62, 390-400.Asymmetric synthesis reaction catalyzed by N-oxide and phosphine oxide.
Makoto Nakajima pp59-70 "New Development of Organocatalysis" Masakatsu Shibasaki Supervision CMC Publishing, 2006.Chiral Phosphine Oxide as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilane.
Nakajima, M .; Kotani, S .; Ishizuka, T .: Hashimoto, S. Tetrahedron Lett. 2005, 46, 157-159.Sterically Congested'Roofed' 2-Thiazolines as New Chiral Ligands for Copper (II)-Catalyzed Asymmetric Diels-Alder Reactions.
Yamakuchi, M .; Matsunaga, H .; Tokuda, R .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Tetrahedron Lett. 2005, 46, 4019-4022.Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO.
Tokuoka, E .; Kotani, S .; Matsunaga, H .; Ishizuka, T .; Hashimoto, S .; Nakajima, M. Tetrahedron: Asymmetry2005, 16, 2391-2392.Sterically Congested'Roofed' 2-Iminothioethers as New Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation.
Tokuda, R .; Matsunaga, H .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Heterocycles 2005, 66, 135-141.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by Chiral N, N'-Dioxides and Monodentate N-Oxides.
Nakajima, M .; Yokota, T .; Saito, M .; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61-64.A New Dirhodium (II) Carboxamidate Complex as a Chiral Lewis Acid Catalyst for Enantioselective Hetero-Diels-Alder Reactions.
Anada, M .; Washio, T .; Shimada, N .; Kitagaki, S .; Nakajima, M .; Shiro, M .; Hashimoto, S. Angew. Chem. Int. Ed. 2004, 43, 2665-2668.The Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate.
Nakajima, M .; Orito, Y .; Ishizuka, T .: Hashimoto, S. Org. Lett .. 2004, 6, 3763-3765.An asymmetric organocatalyst that functions as a Lewis base.
Makoto Nakajima, Chemistry and Chemicals, 2004, 57, 720-723.
Research achievements
Publication
CHIRAL PHOSPHINE OXIDE-CATALYZED ENANTIOSELECTIVE RING OPENING OF OXETANES
Kotani, S .; Tashima, Y .; Tanaka, H .; Aoki, S .; Nakajima M.
Heterocycles, In press.Synthesis of conjugated multiunsaturated thioesters via one-pot TiCl4-promoted aldol condensation.
Boateng, A .; Harada, T .; Ashikari, Y .; Nakajima, M .; Sugiura, M.
Tetrahedron Lett. 2020 , 61 , 152280.Phosphine-oxide-catalyzed Enantioselective Cross-aldol Reaction of Aldehydes with Trichlorosilane as Lewis Acid Promoter.
Kotani, S .; Hanamure, T .; Mori, Y .; Nakajima, M. ChemCat Chem 2020, 12, 4780–4783 ..O -Monoacyltartaric Acid / (Thio) urea Cooperative Organocatalysis for Enantioselective Conjugate Addition of Boronic Acid.
Yoshimitsu, T. Kuboyama, Y. Nishiguchi, S. Nakajima, M. Sugiura, M. Org. Lett. 2020 , 22 , 3780-3784.Recent Advances in Asymmetric Phosphine Oxide Catalysis.
Kotani, S .; Nakajima, M. Tetrahedron Lett . 2020 , 61, 151421.
2019
Lewis Base-catalyzed Enantioselective Conjugate Reductions of β, β-Disubstituted α, β-Unsaturated Ketones with Trichlorosilane: E / Z Isomerization, Regioselectivity, and Synthetic Applications.
Sugiura, M .; Ashikari, Y .; Takahashi, Y .; Yamaguchi, K .; Kotani, S .; Nakajima, M. J. Org. Chem. 2019, 84, 11458-11473.
Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts.
Hashimoto, Y .; Michimuko, C .; Yamaguchi, K .; Nakajima, M .; Sugiura, M. J. Org. Chem. 2019, 84, 9313-9321.
Stereoselective Synthesis of 2-Fluoro-1,3-diols via Lithium Binaphtholate-catalyzed Aldol-Tishchenko Reaction.
Asano, T .; Kotani, S .; Nakajima, M. Org. Lett 2019, 21, 4192-4196.
Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Shimoda, Y .; Nakajima, M. Chem. Pharm. Bull. 2019, 67, 452-446.
2018
Catalytic Enantioselective Aldol Reactions of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis.
Kotani, S .; Yoshiwara, Y .; Ogasawara, M .; Sugiura, M .; Nakajima, M. Angew. Chem. Int. Ed. 2018, 57, 15877-15881.
Dramatic Enantioselectivity Reversal in the Propargylation of Aldehyde with Alkynyllithium Catalyzed by Dilithium Binaphtholate Derivatives.
Nakajima, M .; Watanabe, R .; Osakama, K .; Sakamoto, M .; Takemoto, D. Kukita, K. Heterocycles 2018, 97, 708-711
2017
Development of asymmetric aldol reaction using phosphine oxide as an organomolecular catalyst.
Makoto Nakajima, Chemical industry 2017, 68, 66-72.
Stereoselective Synthesis of Nitrogen-containing Compounds from Enamines.
Sugiura, M .; Kashiwagi, T .; Ito, M .; Kotani, S .; Nakajima, M. J. Org. Chem. 2017, 82, 10968-10979.
Asymmetric Aldol / Vinylogous Aldol / Cyclization Reaction Using Phosphine Oxide Catalysts.
Alim, NR; Miyazaki, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Kotani, S. Chem. Pharm. Bull. 2017, 65, 989-993.
Chiral Lithium Binaphtholate for Enantioselective Amination of Acyclic α-Alkyl-β-keto Esters: Application to the Total Synthesis of L-Carbidopa.
Asano, T .; Moritani, M .; Nakajima. M .; Kotani, S. Tetrahedron 2017, 73, 5975-5982.
Sequential Catalysis of Phosphine Oxide for Stereoselective Synthesis of Stereopentads.
Kotani, S .; Kai, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2017, 19, 3672-3675.
Enantioselective Chlorinative Aldol Reaction of α-Substituted Acroleins Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Hanamure, T .; Nozaki, H .; Sugiura, M .; Nakajima, M. Tetrahedron Asymmetry 2017, 28, 282-287.
2016
Enantioselective Michael Addition of a Malonate Ester to a Maleate Ester Catalyzed by Lithium Binaphtholate.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Nakajima, M. Synlett 2016, 27, 2477-2780.
Enantioselective Amination of Acyclic α-Alkylated β-Keto Esters Catalyzed by Chiral Lithium Binaphtholate.
Kotani, S .; Asano, T .; Moritani, M .; Nakajima, M. Tetrahedron Lett. 2016, 57, 4217-4219.
Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones.
Osakama, K .; Nakajima, M. Org. Lett. 2016, 18, 236-239.
Stereoselective Synthesis of Highly Functionalized 2,3-Dihydro-4-pyranones Using Phosphine Oxide as Catalyst.
Kotani, S .; Miyazaki, S .; Kawahara, K .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Chem. Pharm. Bull. 2016, 64, 189-192.
Concise Asymmetric Construction of C2-Symmetric 1,9-Diarylnonanoids Using Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone.
Kotani, S., Kai, K., Shimoda, Y., Hu, H., Gao, S., Sugiura, M., Ogasawara, M. & Nakajima, M.Chem. Asian J.2016, 11, 376-379.
Indoxyl Sulfate Potentiates Skeletal Muscle Atrophy by Inducing the Oxidative Stress-mediated Expression of Myostatin and Atrogin-1.
Enoki, Y .; Watanabe H .; Arake, R .; Sugimoto, R .; Imafuku, T .; Tominaga, Y .; Ishima, Y .; Kotani, S .; Nakajima, M .; Tanaka, M .; Matsushita , K .; Fukagawa, M .; Otagiri, M .; Maruyama, T. Sci. Rep. 2016, 6, 32084.
2015
Tertiary Amine as a Nucleophile Carrier: α-Aminonitrile in the Cyanation of Acetals and Orthoesters.
Kotani, S .; Sakamoto, M .; Osakama, K .; Nakajima, M. Eur. J. Org. Chem. 2015, 30, 6606-6609.
One-pot Synthesis of β, β-Disubstituted α, β-Unsaturated Carbonyl Compounds using Sequential Ti-Aldol Addition to Ketones and Elimination.
Sugiura, M .; Ashigari, Y .; Nakajima, M. J. Org. Chem. 2015, 80, 8830-8835.
Nitration of Indoxyl Sulfate Facilitates Its Cytotoxicity in Human Renal Proximal Tubular Cells via Expression of Heme Oxygenase-1.
Ishima, Y .; Narisoko, T .; Kragh-Hansen, U .; Kotani, S .; Nakajima, M .; Otagiri, M .; Maruyama, T. Biochemi. Biophys. Res. Commun. 2015, 465, 481-487
Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acid.
Sugiura, M .; Ishikawa, W .; Kuboyama, Y .; Nakajima, M. Synthesis 2015, 47, 2265-2269.
Chiral Lithium Binaphtholate for Enantioselective Michael Addition of Acyclic α-Alkyl-β-keto Esters to Vinyl Ketones.
Kotani, S .; Moritani, M .; Nakajima, M. Asian J. Org. Chem. 2015, 4, 616-618.
-2014
Phosphine Oxide-Catalyzed Enantioselective Intramolecular Aldol Reaction via Regioselective Enolization of Unsymmetrical Diketones with Tetrachlorosilane.
Kotani, S .; Aoki, S .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Org. Lett. 2014, 16, 4802-4805.O-Monoacyltartaric Acid-Catalyzed Enantioselective Conjugate Addition of a Boronic Acid to Dienones: Application to the Synthesis of Optically Active Cyclopentenones.
Sugiura, M .; Kinoshita, R .; Nakajima, M. Org. Lett. 2014, 16, 5172-5175.Human Organic Anion Transporters Function as a High-capacity Transporter for p-Cresyl Sulfate, a Uremic Toxin.
Watanabe, H .; Sakaguchi, Y .; Sugimoto, R .; Kaneko, K .; Iwata, H .; Kotani, S .; Nakajima, M .; Ishima, Y .; Otagiri, M .; Maruyama, T. Clinical and Experimental Nephrology 2014, 18, 814-820.Imino Ene-type Reaction of Enamines with N-Sulfonylimines and Application to Diastereoselective Synthesis of 1,3-Diamines.
Itoh, M .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 4082-4085.Lithium Binaphtholate-catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds.
Kotani, S .; Kukita, K .; Tanaka, K .; Ichibakase, T .; Nakajima, M. J. Org. Chem. 2014, 79, 4809-4816.Diastereoselective Synthesis of 1,3-Diamines by a Domino Reaction of Imines, Enamines, and Trichlorosilane.
Kashiwagi, T .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 1924-1926.Enantioselective Double Aldol Reactions Involving the Sequential Activation of Silicon Tetrachloride by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima, M. Synlett 2014, 25, 631-640.Skeleton construction utilizing continuous aldol reaction-Development to stereoselective polyol synthesis-.
Shunsuke Kotani, Masaharu Sugiura, Makoto Nakajima Chemistry 2013, 68, 64-65.Atropisomeric Chiral Diene in Asymmetric Catalysis: C2-Symmetric (Z, Z) -2, 3-Bis [1- (diphenylphosphinyl) ethylidene] tetralin as Highly Active Lewis Base Organocatalyst.
Ogasawara, M .; Kotani, S .; Nakajima, H .; Furusho, H .; Miyasaka, M .; Shimoda, Y .; Wu, W.-Y .; Sugiura, M .; Takahashi, T .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 13798-13802.Enantioselective Morita–Baylis–Hillman Reaction Catalyzed by a Chiral Phosphine oxide.
Kotani, S .; Itoh, M .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Tetrahedron Lett. 2013, 54, 6430-6433.Enantioselective Aldol Reaction Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima. Chem. Rec. 2013, 13, 362-370.Stereoselective Synthesis of Multiple Stereocenters by Using a Double Aldol Reaction.
Shimoda, Y .; Kubo, T .; Sugiura, M .; Kotani, S .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 3461-3464.Facile Synthesis of Chiral 1,2-Chlorohydrins via the Ring-opening of meso-Epoxides Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Furusho, H .; Tokuoka, E. Nakajima, M. Tetrahedron 2013, 69, 3075-3081.Enantioselective Aldol Reactions Catalyzed by Chiral Lewis Bases.
Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 4, pp 198-209.Allylations of C–O and C–N Double Bonds and Related Reactions.
Sugiura, M .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 214-233.C–X Bond Formation: Organocatalytic Enantioselective Halogenation of meso Epoxides.
Kotani, S .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 506-517.Interaction between Two Sulfate-Conjugated Uremic Toxins, p-Cresyl Sulfate and Indoxyl Sulfate, during Binding with Human Serum Albumin.
Watanabe, H .; Noguchi, T .; Miyamoto, Y .; Kadowaki. D .; Kotani, S .; Nakajima, M .; Miyamura, S .; Ishima, Y .; Otagiri, M .; Maruyama, T. Drug Metab. Dispos. 2012, 40, 1423-1428.Efficient Preparation of 1,3-Diol derivatives with Three Contiguous Stereocenters by an Enantioselective Direct Aldol-Tishchenko Reaction.
Ichibakase, T .; Nakajima, M. Synthesis 2012, 44, 3145-3151.Enantioselective Reductive Aldol Reaction using Teriary Amine as Hydride Donor
Kotani, S .; Osakama, K .: Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2012, 53, 4199-4201.Synthesis of Aryl Group-modified DIOP Dioxides (Ar-DIOPOs) and Their Application as Modular Lewis Base Catalysts.
Ohmaru, Y .; Sato, N .; Mizutani, M .; Kotani, S .; Sugiura, M .; Nakajima, M. Org. Biomol. Chem. 2012, 10, 4562-4570.Trichlorosilyl Triflate Mediated-Enantioselective Directed Cross-Aldol Reaction between Ketones using Chiral Phosphine Oxide as an Organocatalyst.
Aoki, S .; Kotani, S .: Sugiura, M .; Nakajima, M. Chem. Commun. 2012, 48, 5524-5526.Construction of Quaternary Carbon Centers by Base-catalyzed Enantioselective Aldol Reaction and Related Reaction of Trimethoxysilyl Enol Ethers.
Ichibakase, T .; Kaneko, T .; Orito, Y .; Kotani, S .; Nakajima, M. Tetrahedron 2012, 68, 4210-4224.Organic Anion Transporters Play an Important Role in the Uptake of p-Cresyl Sulfate, a Uremic Toxin, in the Kidney.
Miyamoto, Y .; Watanabe, H .; Noguchi, T .; Kotani, S .; Nakajima, M .; Kadowaki, D .; Otagiri, M .; Maruyama, T. Nephrology Dialysis Transplantation 2011, 26, 2498-2502.A Tertiary Amine as A Hydride Donor: Trichlorosilyl Triflate-mediated Conjugate Reduction of Unsaturated Ketones.
Kotani, S .; Osakama, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2011, 13, 3968-3971.Enantioselective Evans-Tishchenko Reduction of β-Hydroxyketone Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Nakatsu, M .; Nakajima, M. Molecules 2011, 52, 5008-5019.Enantioselective Double Aldol Reaction Catalyzed by Chiral Phosphine Oxide.
Shimoda, Y .; Kotani, S .; Sugiura, M .; Nakajima, M. Chem. Eur. J. 2011, 17, 7992-7995.Trichlorosilyl Triflate for Enantioselective Direct-type Aldol Reaction with Chiral Phosphine Oxide.
Kotani, S .; Aoki, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2011, 52, 2834-2836.Lithium Acetylides as Alkynylating Reagents for the Enantioselective Alkynylation of Ketones Catalyzed by Lithium Binaphtholate.
Tanaka, K .; Kukita, K .; Ichibakase, T .; Kotani, S .; Nakajima, M. Chem Commun. 2011, 47, 5614-5616.Direct Enantioselective Aldol-Tishchenko Reaction Catalyzed by Chiral Lithium Diphenylbinaphtholate.
Ichibakase, T .; Nakajima, M. Org. Lett. 2011, 13, 1579-1581.Synthesis of γ-Amino Alcohols from Aldehydes, Enamines, and Trichlorosilane using Lewis Base Catalysts.
Kashiwagi, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2011, 67, 531-539.Enantioselective Conjugate Addition of Boronic Acids to Enones Catalyzed by O-Monoacyltartaric Acids.
Sugiura, M .; Tokudomi, M .; Nakajima, M.Chem. Commun. 2010, 46, 7799-7800.Enantioselective Alkynylation of Carbonyl Compounds with Trimethoxysilylalkynes Catalyzed by Lithium Binaphtholate.
Ueda, T .; Tanaka, K .; Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron 2010, 66, 7726-7731.“Roofed” β-Iminodisulfides as New Chiral Ligands for Palladium-Catalyzed, Asymmetric Allylic Alkylation.
Matsunaga, H .; Tokuda, R .; Nakajima, M .; Ishizuka, T. Chem. Pharm. Bull. 2010, 58, 1419-1421.Development of a direct asymmetric aldol reaction catalyzed by an organic oxide compound.
Makoto Nakajima, Chemical Industry, 2010, 61, 662-666.Development of Chiral Dinitrones as Modular Lewis Base Catalysts: Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes.
Oh, YS; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry 2010, 21, 1833-1835.DMAP-catalyzed Cyanation of Aldehydes and Ketones with Ethyl Cyanoformate.
Aoki, S .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2010, 51, 3547-3549.Enantioselective Alkynylation of Ketones with Trimethoxysilylalkynes using Lithium Binaphtholate as a Catalyst.
Tanaka, K .; Ueda, T .; Ichibakase, T .; Nakajima, M. Tetrahedron Lett. 2010, 51, 2168-2169.Diastereo- and Enantioselective Reductive Aldol Reaction with Trichlorosilane Using Chiral Lewis Bases as Organocatalysts.
Sugiura, M .; Sato, N .; Sonoda, Y .; Kotani, S .; Nakajima .; M. Chem. Asian J. 2010, 5, 478-481.Aldol reaction to build quaternary asymmetric carbon.
Makoto Nakajima, pp 248-249 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Enone's asymmetric reducing aldol reaction.
Masaharu Sugiura, Makoto Nakajima, pp 472-473 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Novel Enantioselective Direct Aldol-type Reaction Promoted by Chiral Phosphine Oxide as an Organocatalyst.
Kotani, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2009, 50, 4602-4605.Enantioselective Aldol Reaction of Silyl Ketene Acetals Promoted by a Lewis Base-activated Lewis Acid Catalyst.
Shimoda, Y .; Tando, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry, 2009, 20, 1369-1370.Asymmetric Synthesis of 4H-1,3-Oxazines: Enantioselective Reductive Cyclization of β-Amino Enones with Trichlorosilane Catalyzed by Chiral Lewis Bases.
Sugiura, M .; Kumahara, M .; Nakajima, M. Chem. Commun. 2009, 3585-3587.Base-catalyzed asymmetric synthesis reaction that activates chlorosilyl compounds.
Makoto Nakajima, pp131-136 "Frontier 21 Evolving Organic Catalyst" Supervised by Keiji Maruoka, Kagaku-Dojin, 2009.A Chiral "Roofed" cis-Diamine-Ru (II) Complex: An Efficient Catalyst for Asymmetric Transfer Hydrogenation of Ketimines.
Matsunaga, H .; Nakanishi, K .; Nakajima, M .; Kunieda, T .; Ishizuka, T. Heterocycles, 2009, 78, 617-622.Lewis Base-catalyzed Conjugate Reduction and Reductive Aldol Reaction of α, β-Unsaturated Ketones Using Trichlorosilane.
Sugiura, M .; Sato, N .; Kotani, S .; Nakajima, M. Chem. Commun. 2008, 4309-4311.Enantioselective Construction of Quaternary Asymmetric Carbon Centers Using an Aldol Reaction of Trimethoxysilyl Enol Ethers Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron Lett. 2008, 49, 4427-4429.First Asymmetric Abramov-type Phosphonylation of Aldehydes with Trialkyl Phosphites Catalyzed by Chiral Lewis Bases.
Nakanishi, K .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2008, 64, 6415-6419.Chiral Phosphine Oxide BINAPO as a Lewis Base Catalyst for Asymmetric Allylation and Aldol Reaction of Trichlorosilyl Compounds.
Kotani, S .; Hashimoto, S .; Nakajima, M. Tetrahedron 2007, 63, 3122-3132.Catalytic Enantioselective Tandem Carbonyl Ylide Formation / 1,3-Dipolar Cycloaddition Reactions of α-Diazo Ketones with Aromatic Aldehydes using Dirhodium (II) Tetrakis [N-benzene-fused-phthaloyl- (S) -valinate].
Tsutsui, H .; Shimada, N .; Abe, T .; Anada, M .; Nakajima, M .; Nakamura, S .; Nambu, H .; Hashimoto, S. Adv. Synth. Catal. 2007, 349, 521-526.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by the Chiral Phosphine Oxide BINAPO.
Kotani, S .; Hashimoto, S .; Nakajima, M. Synlett 2006, 1116-1118.Lewis Base Catalyzed Asymmetric Reactions Involving Hypervalent Silicate Intermediates.
Orito, Y .; Nakajima, M. Synthesis 2006, 1391-1401.Chiral Base-Catalyzed Aldol Reaction of Trimethoxysilyl Enol Ethers: Effect of Water as an Additive on Stereoselectivities.
Orito, Y .; Hashimoto, S .; Ishizuka, T .; Nakajima, M. Tetrahedron 2006, 62, 390-400.Asymmetric synthesis reaction catalyzed by N-oxide and phosphine oxide.
Makoto Nakajima pp59-70 "New Development of Organocatalysis" Masakatsu Shibasaki Supervision CMC Publishing, 2006.Chiral Phosphine Oxide as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilane.
Nakajima, M .; Kotani, S .; Ishizuka, T .: Hashimoto, S. Tetrahedron Lett. 2005, 46, 157-159.Sterically Congested'Roofed' 2-Thiazolines as New Chiral Ligands for Copper (II)-Catalyzed Asymmetric Diels-Alder Reactions.
Yamakuchi, M .; Matsunaga, H .; Tokuda, R .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Tetrahedron Lett. 2005, 46, 4019-4022.Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO.
Tokuoka, E .; Kotani, S .; Matsunaga, H .; Ishizuka, T .; Hashimoto, S .; Nakajima, M. Tetrahedron: Asymmetry2005, 16, 2391-2392.Sterically Congested'Roofed' 2-Iminothioethers as New Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation.
Tokuda, R .; Matsunaga, H .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Heterocycles 2005, 66, 135-141.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by Chiral N, N'-Dioxides and Monodentate N-Oxides.
Nakajima, M .; Yokota, T .; Saito, M .; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61-64.A New Dirhodium (II) Carboxamidate Complex as a Chiral Lewis Acid Catalyst for Enantioselective Hetero-Diels-Alder Reactions.
Anada, M .; Washio, T .; Shimada, N .; Kitagaki, S .; Nakajima, M .; Shiro, M .; Hashimoto, S. Angew. Chem. Int. Ed. 2004, 43, 2665-2668.The Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate.
Nakajima, M .; Orito, Y .; Ishizuka, T .: Hashimoto, S. Org. Lett .. 2004, 6, 3763-3765.An asymmetric organocatalyst that functions as a Lewis base.
Makoto Nakajima, Chemistry and Chemicals, 2004, 57, 720-723.
Research achievements
Publication
2021
Catalysis with Earth-abundant Elements; CHAPTER 11: Catalysis by Silicon Species
Sugiura, M .; Kotani, S .; Nakajima, M.
RSC Catalysis Series 2021-January (40) 309-333 2021CHIRAL PHOSPHINE OXIDE-CATALYZED ENANTIOSELECTIVE RING OPENING OF OXETANES
Kotani, S .; Tashima, Y .; Tanaka, H .; Aoki, S .; Nakajima M. 2021 , 103 , 1048–1056,
Heterocycles, In press.
2020
Synthesis of conjugated multiunsaturated thioesters via one-pot TiCl4-promoted aldol condensation.
Boateng, A .; Harada, T .; Ashikari, Y .; Nakajima, M .; Sugiura, M.
Tetrahedron Lett. 2020 , 61 , 152280.Phosphine-oxide-catalyzed Enantioselective Cross-aldol Reaction of Aldehydes with Trichlorosilane as Lewis Acid Promoter.
Kotani, S .; Hanamure, T .; Mori, Y .; Nakajima, M. ChemCat Chem 2020, 12, 4780–4783 ..O -Monoacyltartaric Acid / (Thio) urea Cooperative Organocatalysis for Enantioselective Conjugate Addition of Boronic Acid.
Yoshimitsu, T. Kuboyama, Y. Nishiguchi, S. Nakajima, M. Sugiura, M. Org. Lett. 2020 , 22 , 3780-3784.Recent Advances in Asymmetric Phosphine Oxide Catalysis.
Kotani, S .; Nakajima, M. Tetrahedron Lett . 2020 , 61, 151421.
2019
Lewis Base-catalyzed Enantioselective Conjugate Reductions of β, β-Disubstituted α, β-Unsaturated Ketones with Trichlorosilane: E / Z Isomerization, Regioselectivity, and Synthetic Applications.
Sugiura, M .; Ashikari, Y .; Takahashi, Y .; Yamaguchi, K .; Kotani, S .; Nakajima, M. J. Org. Chem. 2019, 84, 11458-11473.
Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts.
Hashimoto, Y .; Michimuko, C .; Yamaguchi, K .; Nakajima, M .; Sugiura, M. J. Org. Chem. 2019, 84, 9313-9321.
Stereoselective Synthesis of 2-Fluoro-1,3-diols via Lithium Binaphtholate-catalyzed Aldol-Tishchenko Reaction.
Asano, T .; Kotani, S .; Nakajima, M. Org. Lett 2019, 21, 4192-4196.
Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Shimoda, Y .; Nakajima, M. Chem. Pharm. Bull. 2019, 67, 452-446.
2018
Catalytic Enantioselective Aldol Reactions of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis.
Kotani, S .; Yoshiwara, Y .; Ogasawara, M .; Sugiura, M .; Nakajima, M. Angew. Chem. Int. Ed. 2018, 57, 15877-15881.
Dramatic Enantioselectivity Reversal in the Propargylation of Aldehyde with Alkynyllithium Catalyzed by Dilithium Binaphtholate Derivatives.
Nakajima, M .; Watanabe, R .; Osakama, K .; Sakamoto, M .; Takemoto, D. Kukita, K. Heterocycles 2018, 97, 708-711
2017
Development of asymmetric aldol reaction using phosphine oxide as an organomolecular catalyst.
Makoto Nakajima, Chemical industry 2017, 68, 66-72.
Stereoselective Synthesis of Nitrogen-containing Compounds from Enamines.
Sugiura, M .; Kashiwagi, T .; Ito, M .; Kotani, S .; Nakajima, M. J. Org. Chem. 2017, 82, 10968-10979.
Asymmetric Aldol / Vinylogous Aldol / Cyclization Reaction Using Phosphine Oxide Catalysts.
Alim, NR; Miyazaki, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Kotani, S. Chem. Pharm. Bull. 2017, 65, 989-993.
Chiral Lithium Binaphtholate for Enantioselective Amination of Acyclic α-Alkyl-β-keto Esters: Application to the Total Synthesis of L-Carbidopa.
Asano, T .; Moritani, M .; Nakajima. M .; Kotani, S. Tetrahedron 2017, 73, 5975-5982.
Sequential Catalysis of Phosphine Oxide for Stereoselective Synthesis of Stereopentads.
Kotani, S .; Kai, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2017, 19, 3672-3675.
Enantioselective Chlorinative Aldol Reaction of α-Substituted Acroleins Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Hanamure, T .; Nozaki, H .; Sugiura, M .; Nakajima, M. Tetrahedron Asymmetry 2017, 28, 282-287.
2016
Enantioselective Michael Addition of a Malonate Ester to a Maleate Ester Catalyzed by Lithium Binaphtholate.
Sakamoto, M .; Kaneko, T .; Orito, Y .; Nakajima, M. Synlett 2016, 27, 2477-2780.
Enantioselective Amination of Acyclic α-Alkylated β-Keto Esters Catalyzed by Chiral Lithium Binaphtholate.
Kotani, S .; Asano, T .; Moritani, M .; Nakajima, M. Tetrahedron Lett. 2016, 57, 4217-4219.
Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones.
Osakama, K .; Nakajima, M. Org. Lett. 2016, 18, 236-239.
Stereoselective Synthesis of Highly Functionalized 2,3-Dihydro-4-pyranones Using Phosphine Oxide as Catalyst.
Kotani, S .; Miyazaki, S .; Kawahara, K .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Chem. Pharm. Bull. 2016, 64, 189-192.
Concise Asymmetric Construction of C2-Symmetric 1,9-Diarylnonanoids Using Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone.
Kotani, S., Kai, K., Shimoda, Y., Hu, H., Gao, S., Sugiura, M., Ogasawara, M. & Nakajima, M.Chem. Asian J.2016, 11, 376-379.
Indoxyl Sulfate Potentiates Skeletal Muscle Atrophy by Inducing the Oxidative Stress-mediated Expression of Myostatin and Atrogin-1.
Enoki, Y .; Watanabe H .; Arake, R .; Sugimoto, R .; Imafuku, T .; Tominaga, Y .; Ishima, Y .; Kotani, S .; Nakajima, M .; Tanaka, M .; Matsushita , K .; Fukagawa, M .; Otagiri, M .; Maruyama, T. Sci. Rep. 2016, 6, 32084.
2015
Tertiary Amine as a Nucleophile Carrier: α-Aminonitrile in the Cyanation of Acetals and Orthoesters.
Kotani, S .; Sakamoto, M .; Osakama, K .; Nakajima, M. Eur. J. Org. Chem. 2015, 30, 6606-6609.
One-pot Synthesis of β, β-Disubstituted α, β-Unsaturated Carbonyl Compounds using Sequential Ti-Aldol Addition to Ketones and Elimination.
Sugiura, M .; Ashigari, Y .; Nakajima, M. J. Org. Chem. 2015, 80, 8830-8835.
Nitration of Indoxyl Sulfate Facilitates Its Cytotoxicity in Human Renal Proximal Tubular Cells via Expression of Heme Oxygenase-1.
Ishima, Y .; Narisoko, T .; Kragh-Hansen, U .; Kotani, S .; Nakajima, M .; Otagiri, M .; Maruyama, T. Biochemi. Biophys. Res. Commun. 2015, 465, 481-487
Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acid.
Sugiura, M .; Ishikawa, W .; Kuboyama, Y .; Nakajima, M. Synthesis 2015, 47, 2265-2269.
Chiral Lithium Binaphtholate for Enantioselective Michael Addition of Acyclic α-Alkyl-β-keto Esters to Vinyl Ketones.
Kotani, S .; Moritani, M .; Nakajima, M. Asian J. Org. Chem. 2015, 4, 616-618.
-2014
Phosphine Oxide-Catalyzed Enantioselective Intramolecular Aldol Reaction via Regioselective Enolization of Unsymmetrical Diketones with Tetrachlorosilane.
Kotani, S .; Aoki, S .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Org. Lett. 2014, 16, 4802-4805.O-Monoacyltartaric Acid-Catalyzed Enantioselective Conjugate Addition of a Boronic Acid to Dienones: Application to the Synthesis of Optically Active Cyclopentenones.
Sugiura, M .; Kinoshita, R .; Nakajima, M. Org. Lett. 2014, 16, 5172-5175.Human Organic Anion Transporters Function as a High-capacity Transporter for p-Cresyl Sulfate, a Uremic Toxin.
Watanabe, H .; Sakaguchi, Y .; Sugimoto, R .; Kaneko, K .; Iwata, H .; Kotani, S .; Nakajima, M .; Ishima, Y .; Otagiri, M .; Maruyama, T. Clinical and Experimental Nephrology 2014, 18, 814-820.Imino Ene-type Reaction of Enamines with N-Sulfonylimines and Application to Diastereoselective Synthesis of 1,3-Diamines.
Itoh, M .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 4082-4085.Lithium Binaphtholate-catalyzed Asymmetric Addition of Lithium Acetylides to Carbonyl Compounds.
Kotani, S .; Kukita, K .; Tanaka, K .; Ichibakase, T .; Nakajima, M. J. Org. Chem. 2014, 79, 4809-4816.Diastereoselective Synthesis of 1,3-Diamines by a Domino Reaction of Imines, Enamines, and Trichlorosilane.
Kashiwagi, T .; Kotani, S .; Nakajima, M .; Sugiura, M. Tetrahedron Lett. 2014, 55, 1924-1926.Enantioselective Double Aldol Reactions Involving the Sequential Activation of Silicon Tetrachloride by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima, M. Synlett 2014, 25, 631-640.Skeleton construction utilizing continuous aldol reaction-Development to stereoselective polyol synthesis-.
Shunsuke Kotani, Masaharu Sugiura, Makoto Nakajima Chemistry 2013, 68, 64-65.Atropisomeric Chiral Diene in Asymmetric Catalysis: C2-Symmetric (Z, Z) -2, 3-Bis [1- (diphenylphosphinyl) ethylidene] tetralin as Highly Active Lewis Base Organocatalyst.
Ogasawara, M .; Kotani, S .; Nakajima, H .; Furusho, H .; Miyasaka, M .; Shimoda, Y .; Wu, W.-Y .; Sugiura, M .; Takahashi, T .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 13798-13802.Enantioselective Morita–Baylis–Hillman Reaction Catalyzed by a Chiral Phosphine oxide.
Kotani, S .; Itoh, M .; Sugiura, M .; Ogasawara, M .; Nakajima, M. Tetrahedron Lett. 2013, 54, 6430-6433.Enantioselective Aldol Reaction Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Sugiura, M .; Nakajima. Chem. Rec. 2013, 13, 362-370.Stereoselective Synthesis of Multiple Stereocenters by Using a Double Aldol Reaction.
Shimoda, Y .; Kubo, T .; Sugiura, M .; Kotani, S .; Nakajima, M. Angew. Chem. Int. Ed. 2013, 52, 3461-3464.Facile Synthesis of Chiral 1,2-Chlorohydrins via the Ring-opening of meso-Epoxides Catalyzed by Chiral Phosphine Oxides.
Kotani, S .; Furusho, H .; Tokuoka, E. Nakajima, M. Tetrahedron 2013, 69, 3075-3081.Enantioselective Aldol Reactions Catalyzed by Chiral Lewis Bases.
Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 4, pp 198-209.Allylations of C–O and C–N Double Bonds and Related Reactions.
Sugiura, M .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 214-233.C–X Bond Formation: Organocatalytic Enantioselective Halogenation of meso Epoxides.
Kotani, S .; Nakajima, M. in “Comprehensive Chirality” Carreira, EM; Yamamoto, H. Eds, Elsevier, 2012, Vol. 6, pp 506-517.Interaction between Two Sulfate-Conjugated Uremic Toxins, p-Cresyl Sulfate and Indoxyl Sulfate, during Binding with Human Serum Albumin.
Watanabe, H .; Noguchi, T .; Miyamoto, Y .; Kadowaki. D .; Kotani, S .; Nakajima, M .; Miyamura, S .; Ishima, Y .; Otagiri, M .; Maruyama, T. Drug Metab. Dispos. 2012, 40, 1423-1428.Efficient Preparation of 1,3-Diol derivatives with Three Contiguous Stereocenters by an Enantioselective Direct Aldol-Tishchenko Reaction.
Ichibakase, T .; Nakajima, M. Synthesis 2012, 44, 3145-3151.Enantioselective Reductive Aldol Reaction using Teriary Amine as Hydride Donor
Kotani, S .; Osakama, K .: Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2012, 53, 4199-4201.Synthesis of Aryl Group-modified DIOP Dioxides (Ar-DIOPOs) and Their Application as Modular Lewis Base Catalysts.
Ohmaru, Y .; Sato, N .; Mizutani, M .; Kotani, S .; Sugiura, M .; Nakajima, M. Org. Biomol. Chem. 2012, 10, 4562-4570.Trichlorosilyl Triflate Mediated-Enantioselective Directed Cross-Aldol Reaction between Ketones using Chiral Phosphine Oxide as an Organocatalyst.
Aoki, S .; Kotani, S .: Sugiura, M .; Nakajima, M. Chem. Commun. 2012, 48, 5524-5526.Construction of Quaternary Carbon Centers by Base-catalyzed Enantioselective Aldol Reaction and Related Reaction of Trimethoxysilyl Enol Ethers.
Ichibakase, T .; Kaneko, T .; Orito, Y .; Kotani, S .; Nakajima, M. Tetrahedron 2012, 68, 4210-4224.Organic Anion Transporters Play an Important Role in the Uptake of p-Cresyl Sulfate, a Uremic Toxin, in the Kidney.
Miyamoto, Y .; Watanabe, H .; Noguchi, T .; Kotani, S .; Nakajima, M .; Kadowaki, D .; Otagiri, M .; Maruyama, T. Nephrology Dialysis Transplantation 2011, 26, 2498-2502.A Tertiary Amine as A Hydride Donor: Trichlorosilyl Triflate-mediated Conjugate Reduction of Unsaturated Ketones.
Kotani, S .; Osakama, K .; Sugiura, M .; Nakajima, M. Org. Lett. 2011, 13, 3968-3971.Enantioselective Evans-Tishchenko Reduction of β-Hydroxyketone Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Nakatsu, M .; Nakajima, M. Molecules 2011, 52, 5008-5019.Enantioselective Double Aldol Reaction Catalyzed by Chiral Phosphine Oxide.
Shimoda, Y .; Kotani, S .; Sugiura, M .; Nakajima, M. Chem. Eur. J. 2011, 17, 7992-7995.Trichlorosilyl Triflate for Enantioselective Direct-type Aldol Reaction with Chiral Phosphine Oxide.
Kotani, S .; Aoki, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2011, 52, 2834-2836.Lithium Acetylides as Alkynylating Reagents for the Enantioselective Alkynylation of Ketones Catalyzed by Lithium Binaphtholate.
Tanaka, K .; Kukita, K .; Ichibakase, T .; Kotani, S .; Nakajima, M. Chem Commun. 2011, 47, 5614-5616.Direct Enantioselective Aldol-Tishchenko Reaction Catalyzed by Chiral Lithium Diphenylbinaphtholate.
Ichibakase, T .; Nakajima, M. Org. Lett. 2011, 13, 1579-1581.Synthesis of γ-Amino Alcohols from Aldehydes, Enamines, and Trichlorosilane using Lewis Base Catalysts.
Kashiwagi, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2011, 67, 531-539.Enantioselective Conjugate Addition of Boronic Acids to Enones Catalyzed by O-Monoacyltartaric Acids.
Sugiura, M .; Tokudomi, M .; Nakajima, M.Chem. Commun. 2010, 46, 7799-7800.Enantioselective Alkynylation of Carbonyl Compounds with Trimethoxysilylalkynes Catalyzed by Lithium Binaphtholate.
Ueda, T .; Tanaka, K .; Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron 2010, 66, 7726-7731.“Roofed” β-Iminodisulfides as New Chiral Ligands for Palladium-Catalyzed, Asymmetric Allylic Alkylation.
Matsunaga, H .; Tokuda, R .; Nakajima, M .; Ishizuka, T. Chem. Pharm. Bull. 2010, 58, 1419-1421.Development of a direct asymmetric aldol reaction catalyzed by an organic oxide compound.
Makoto Nakajima, Chemical Industry, 2010, 61, 662-666.Development of Chiral Dinitrones as Modular Lewis Base Catalysts: Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes.
Oh, YS; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry 2010, 21, 1833-1835.DMAP-catalyzed Cyanation of Aldehydes and Ketones with Ethyl Cyanoformate.
Aoki, S .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2010, 51, 3547-3549.Enantioselective Alkynylation of Ketones with Trimethoxysilylalkynes using Lithium Binaphtholate as a Catalyst.
Tanaka, K .; Ueda, T .; Ichibakase, T .; Nakajima, M. Tetrahedron Lett. 2010, 51, 2168-2169.Diastereo- and Enantioselective Reductive Aldol Reaction with Trichlorosilane Using Chiral Lewis Bases as Organocatalysts.
Sugiura, M .; Sato, N .; Sonoda, Y .; Kotani, S .; Nakajima .; M. Chem. Asian J. 2010, 5, 478-481.Aldol reaction to build quaternary asymmetric carbon.
Makoto Nakajima, pp 248-249 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Enone's asymmetric reducing aldol reaction.
Masaharu Sugiura, Makoto Nakajima, pp 472-473 "Usable! Organic Synthesis Reaction 241 Practical Guide" Keiji Maruoka, Kyoko Nozaki, Yasutaka Ishii, Junzo Odera, Kiyoshi Tomioka, Kagaku-Dojin, 2010.Novel Enantioselective Direct Aldol-type Reaction Promoted by Chiral Phosphine Oxide as an Organocatalyst.
Kotani, S .; Shimoda, Y .; Sugiura, M .; Nakajima, M. Tetrahedron Lett. 2009, 50, 4602-4605.Enantioselective Aldol Reaction of Silyl Ketene Acetals Promoted by a Lewis Base-activated Lewis Acid Catalyst.
Shimoda, Y .; Tando, T .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron: Asymmetry, 2009, 20, 1369-1370.Asymmetric Synthesis of 4H-1,3-Oxazines: Enantioselective Reductive Cyclization of β-Amino Enones with Trichlorosilane Catalyzed by Chiral Lewis Bases.
Sugiura, M .; Kumahara, M .; Nakajima, M. Chem. Commun. 2009, 3585-3587.Base-catalyzed asymmetric synthesis reaction that activates chlorosilyl compounds.
Makoto Nakajima, pp131-136 "Frontier 21 Evolving Organic Catalyst" Supervised by Keiji Maruoka, Kagaku-Dojin, 2009.A Chiral "Roofed" cis-Diamine-Ru (II) Complex: An Efficient Catalyst for Asymmetric Transfer Hydrogenation of Ketimines.
Matsunaga, H .; Nakanishi, K .; Nakajima, M .; Kunieda, T .; Ishizuka, T. Heterocycles, 2009, 78, 617-622.Lewis Base-catalyzed Conjugate Reduction and Reductive Aldol Reaction of α, β-Unsaturated Ketones Using Trichlorosilane.
Sugiura, M .; Sato, N .; Kotani, S .; Nakajima, M. Chem. Commun. 2008, 4309-4311.Enantioselective Construction of Quaternary Asymmetric Carbon Centers Using an Aldol Reaction of Trimethoxysilyl Enol Ethers Catalyzed by Lithium Binaphtholate.
Ichibakase, T .; Orito, Y .; Nakajima, M. Tetrahedron Lett. 2008, 49, 4427-4429.First Asymmetric Abramov-type Phosphonylation of Aldehydes with Trialkyl Phosphites Catalyzed by Chiral Lewis Bases.
Nakanishi, K .; Kotani, S .; Sugiura, M .; Nakajima, M. Tetrahedron 2008, 64, 6415-6419.Chiral Phosphine Oxide BINAPO as a Lewis Base Catalyst for Asymmetric Allylation and Aldol Reaction of Trichlorosilyl Compounds.
Kotani, S .; Hashimoto, S .; Nakajima, M. Tetrahedron 2007, 63, 3122-3132.Catalytic Enantioselective Tandem Carbonyl Ylide Formation / 1,3-Dipolar Cycloaddition Reactions of α-Diazo Ketones with Aromatic Aldehydes using Dirhodium (II) Tetrakis [N-benzene-fused-phthaloyl- (S) -valinate].
Tsutsui, H .; Shimada, N .; Abe, T .; Anada, M .; Nakajima, M .; Nakamura, S .; Nambu, H .; Hashimoto, S. Adv. Synth. Catal. 2007, 349, 521-526.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by the Chiral Phosphine Oxide BINAPO.
Kotani, S .; Hashimoto, S .; Nakajima, M. Synlett 2006, 1116-1118.Lewis Base Catalyzed Asymmetric Reactions Involving Hypervalent Silicate Intermediates.
Orito, Y .; Nakajima, M. Synthesis 2006, 1391-1401.Chiral Base-Catalyzed Aldol Reaction of Trimethoxysilyl Enol Ethers: Effect of Water as an Additive on Stereoselectivities.
Orito, Y .; Hashimoto, S .; Ishizuka, T .; Nakajima, M. Tetrahedron 2006, 62, 390-400.Asymmetric synthesis reaction catalyzed by N-oxide and phosphine oxide.
Makoto Nakajima pp59-70 "New Development of Organocatalysis" Masakatsu Shibasaki Supervision CMC Publishing, 2006.Chiral Phosphine Oxide as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilane.
Nakajima, M .; Kotani, S .; Ishizuka, T .: Hashimoto, S. Tetrahedron Lett. 2005, 46, 157-159.Sterically Congested'Roofed' 2-Thiazolines as New Chiral Ligands for Copper (II)-Catalyzed Asymmetric Diels-Alder Reactions.
Yamakuchi, M .; Matsunaga, H .; Tokuda, R .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Tetrahedron Lett. 2005, 46, 4019-4022.Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO.
Tokuoka, E .; Kotani, S .; Matsunaga, H .; Ishizuka, T .; Hashimoto, S .; Nakajima, M. Tetrahedron: Asymmetry2005, 16, 2391-2392.Sterically Congested'Roofed' 2-Iminothioethers as New Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation.
Tokuda, R .; Matsunaga, H .; Ishizuka, T .; Nakajima, M .; Kunieda, T. Heterocycles 2005, 66, 135-141.Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by Chiral N, N'-Dioxides and Monodentate N-Oxides.
Nakajima, M .; Yokota, T .; Saito, M .; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61-64.A New Dirhodium (II) Carboxamidate Complex as a Chiral Lewis Acid Catalyst for Enantioselective Hetero-Diels-Alder Reactions.
Anada, M .; Washio, T .; Shimada, N .; Kitagaki, S .; Nakajima, M .; Shiro, M .; Hashimoto, S. Angew. Chem. Int. Ed. 2004, 43, 2665-2668.The Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate.
Nakajima, M .; Orito, Y .; Ishizuka, T .: Hashimoto, S. Org. Lett .. 2004, 6, 3763-3765.An asymmetric organocatalyst that functions as a Lewis base.
Makoto Nakajima, Chemistry and Chemicals, 2004, 57, 720-723.