原著論文

(66) Silylative Kinetic Resolution of Acyclic Secondary Benzylic Alcohols Catalyzed by Chiral Guanidine Having Axial Chirailty Containing a Methoxy Group. Y. Homma, T. Ikeue, K. Nakata. Chinese Journal of Chemistry 2025, 43, 1553–1559. https://doi.org/10.1002/cjoc.70025 [Open Access]

(65) Enantioselecyive Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines. A. Ui, M. Iwakura, S. Yoshimatsu, K. Nakata. Synlett 2025, 36, 279–283. [Selected as the Cover Graphic].https://doi.org/10.1055/a-2322-0904

(64) A Facile Preparation of Tetrasubstituted Arylalkenes Catalyzed by p-Toluenesulfonic Acid Monohydrate
(p-TsOH·H2O): Application in the Synthesis of the Intermediate of Tamoxifen. T. Sutani, N. Kimura, K. Nakata. ChemistrySelect 2024, 9, e20240295. https://doi.org/10.1002/slct.202402951

(63) Acylative and Silylative Dynamic Kinetic Resolutions of 6-Hydroxy-2H-pyran-3(6H)-one Catalyzed by Chiral Guanidines. K. Miyazaki, K. Nakata. Synlett 2024, 35, 1591–1595. [Featured in Org. Chem. Highlights, May 12th].https://doi.org/10.1055/a-2206-7545​

(62) Diastereoselective Cross-Dehydrogenative Coupling Reactions of Amides with Diarylmethanes Using DDQ through C–H Benzylic Activation. N. Kimura, K. Nakata. Synlett 2024, 35, 240–244. https://doi.org/10.1055/a-2182-7532

(61) Design and Synthesis of Axial-Chirality-Containing Guanidine Catalysts. M. Iwakura, T. Ikeue, K. Nakata. ChemistrySelect 2022, 7, e202202511. https://doi.org/10.1002/slct.202202511

(60) Two-Step Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using the Combination of Enantioselective Silylation and Acylation: One-Pot Procedure Catalyzed by Chiral Guanidine. K. Miyazaki, K. Nakata. The Journal of Organic Chemistry.2022, 87, 10509–10515. https://doi.org/10.1021/acs.joc.2c01129

(59) FeCl3-catalyzed Diastereodivergent Sulfamidation of Diarylmethanol Diastereomixtures Bearing a Chiral Auxiliary Dependent on Catalyst Loading. R. Oda, H. Yamamoto, K. Nakata..Asian Journal of Organic Chemistry.2021, 10, 3266–3270. https://doi.org/10.1002/ajoc.202100605

(58) Highly Efficient Silylative Kinetic Resolution of Racemic trans-2-Alkyl-1-indanols Catalyzed by Chiral Guanidine. T. Suzuki, M. Iwakura, K. Nakata. ChemistrySelect.2021, 6, 11261–11264. https://doi.org/10.1002/slct.202103341

(57) Chiral Guanidine Catalyzed Acylative Kinetic Resolution of Racemic 2-Bromo-1-arylethanols. E. Sawada, K. Nakata. Chemistry Letters.2021, 50, 371–373. https://doi.org/10.1246/cl.200786

(56) Lewis Acid-Catalyzed Nucleophilic Substitutions of Benzylic Alcohols with Sulfamides. R. Oda, K. Nakata. European Journal of Organic Chemistry.2021, 2021, 295–301. https://doi.org/10.1002/ejoc.202001320

(55) Chemodiergent Dehydrative Nucleophilic Substitutions of Diarylmethanols with 1-Phenyl-1H-tetrazole-5-thiol Catalyzed by FeCl3. R. Oda, K. Nakata. Asian Journal of Organic Chemistry.2020, 9, 1234–1242.  https://doi.org/10.1002/ajoc.202000301

(54) Kinetic Resolution of Racemic 2-Hydroxyketones by Asymmetric Esterification: Investigation of the Influence of the Co-base on the Selectivity. T. Murata, K. Futami, R. Ishikawa, K. Ono, K. Nakata, I. Shiina. Asian Journal of Organic Chemistry.2020, 2, 202–205. https://doi.org/10.1002/ajoc.201900702

(53) Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3-Dicarbonyls Catalyzed by SnBr4. R. Kubo, H. Yamamoto, K. Nakata. European Journal of Organic Chemistry.2019, 2019, 7394–7398. https://doi.org/10.1002/ejoc.201901377

(52) Silylative Kinetic Resolutionof Racemic 2,2-Dialkyl 5-and 6-Membered Cyclic Benzylic Alcohol Derivatives Catalyzed by Chiral Guanidine, (R)-N-Methylbenzoguanidine. S. Yoshimatsu, K. Nakata. Advanced Synthesis & Catalysis.2019, 361, 4679–4684. https://doi.org/10.1002/adsc.201900761

(51) Acylative Kinetic Resolution of Racemic 2,2-Dimethyl Substituted Nitroaldol (Henry) Adducts Using a Chiral Guanidine Catalyst: (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG). T. Ichimura, R. Kishida, K. Nakata..ChemistrySelect.2019, 4, 9440–9443. https://doi.org/10.1002/slct.201902236

(50) Diastereoconergent Synthesis of Chiral Diarylmethyl Sulfones by Direct Sulfonylation of Diarylmethanols Diastereomixtures with Sodium Sulfinates Catalyzed by SnBr2. H. Yamamoto, K. Nakata. European Journal of Organic Chemistry.2019, 2019, 4906–4910. https://doi.org/10.1002/ejoc.201900830

(49) Novel Ridaifen-B Structure Analog Induces Apoptosis and Autophagy Depending on Pyrrolidine Side Chain. T. Iwasawa, T. Shinomiya, N. Ota, N. Shibata, K. Nakata, I. Shiina, Y. Nagahara. Biological Pharmaceutical Bulltin.2019, 42, 401–410. https://doi.org/10.1248/bpb.b18-00643

(48) Reformatsky Reagent Promoted Acetylation of Primary and Secondary Aliphatic Alcohols Using Ethyl Acatate as an Acetyl Donor. R. Fujihara, K. Nakata. ChemistrySelect.2019, 4, 75–77. https://doi.org/10.1002/slct.201803162

(47) Chiral-Auxiliary-Controlled Diastereoconvergent Benzamidation Reactions of Diastereomixtures of Diarylmethanols with Benzamide Catalyzed by SnBr4. R. Kubo, K. Nakata. Asian Journal of Organic Chemistry.2019, 8, 119–122.  https://doi.org/10.1002/ajoc.201800635

(46) Stereoconvergent Chiral Inductive Diastereodivergent Sulfonamidation of Diastereomixtures of Diarylmethanols with Sulfonylamine Catalyzed by Lewis Acids. H. Yamamoto, K. Nakata. Organic Letters.2018, 20, 7057–7061.  https://doi.org/10.1021/acs.orglett.8b03008

(45) Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3. R. Fujihara, K. Nakata. European Journal of Organic Chemistry.2018, 2018, 6566–6573. https://doi.org/10.1002/ejoc.201801236

(44) Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst. T. Murata, T. Kawanishi, A. Sekiguchi, R. Ishikawa, K. Ono, K. Nakata, I. Shiina. Molecules.2018, 23, 2003. https://doi.org/10.3390/molecules23082003

(43) Silylative Kinetic Resolution of Racemic 1-Indanol Derivatives Catalyzed by Chiral Guanidine. S. Yoshimatsu, A. Yamada, K. Nakata. The Journal of Organic Chemistry.2018, 83, 452–458. https://doi.org/10.1021/acs.joc.7b02493

(42) Chiral Inductive Diastereoconvergent Friedel–Crafts Alkylation Reaction of Diastereomixtures of Diarylmethanols with 2-Naphthol Derivatives Catalyzed by SnBr4. N. Suzuki, K. Nakata. European Journal of Organic Chemistry.2017, 2017 7075–7086. https://doi.org/10.1002/ejoc.201701280

(41) Acylative Kinetic Resolution of Racemic Aromatic β-Hydroxy Esters Catalyzed by Chiral Nucleophilic N-(1-Arylethyl)benzoguanidines. A. Yamada, K. Nakata, I. Shiina. Tetrahedron: Asymmetry.2017, 28, 516–521.  https://doi.org/10.1016/j.tetasy.2017.03.005

(40) Chemoselective N-Acetylation of Primary Aliphatic Amines Promoted by Pivalic Acid or Acetic Acid Using Ethyl Acetate as an Acetyl Donor. T. Yoshida, S. Kawamura, K. Nakata. Tetrahedron Letters.2017, 58, 1181–1184.  https://doi.org/10.1016/j.tetlet.2017.02.015

(39) Kinetic Resolution of Racemic 2-Hydroxyacetals by the Asymmetric Esterification Using Mixed Anhydride Protocal. K. Nakata, E. Tokumaru, T. Saitoh, T. Nakahara, K. Ono, T. Murata, I. Shiina. Heterocycles.2017, 95, 277–289.

(38) (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) Catalyzed Acylative Kinetic Resolution of Racemic 3-Hydroxy-3-aryl-propanoates. A. Yamada, K. Nakata. Tetrahedron Letters.2016, 57, 4697–4701.  https://doi.org/10.1016/j.tetlet.2016.09.014

(37) SnBr4-Promoted Friedel–Crafts Type Dehydrative Alkylation Reaction of Diarylmethanols with 2-Naphthol Derivatives. N. Suzuki, S. Tsuchihashi, K. Nakata. Tetrahedron Letters.2016, 57, 1456–1459.  https://doi.org/10.1016/j.tetlet.2016.02.064

(36) InCl3-Promoted Intramolecular Decarboxylative Etherification of Benzylic Carbonates. T. Tokumaru, K. Nakata. Tetrahedron Letters.2015, 56, 2336–2339. https://doi.org/10.1016/j.tetlet.2015.03.088

(35) Acceleration of CuI-Catalyzed Coupling Reaction of Alkyl Halides with Aryl Grignard Reagents Using Lithium Chloride. K. Nakata, C. Feng, T. Tojo, Y. Kobayashi. Tetrahedron Letters.2014, 55, 5774–5777.

(34) A Novel Tamoxifen Derivatives, Ridaifen-F, is a Nonpeptidic Small-Molecular Inhibitor. M. Hasegawa, Y. Yasuda, M. Tanaka, K. Nakata, E. Umeda, Y. Wang, C. Watanabe, S. Uetake, T. Kunoh, M. Shionyu, R. Sasaki, I. Shiina, T. Mizukami.European Journal of Medicinal Chemistry.2014, 70, 290–305.

(33) An Enantiodivergent Synthesis of (+)- and (–)-Centrolobines by Asymmetric Esterification Catalyzed by (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG). K. Nakata, T. Tokumaru, H. Iwamoto, Y. Nishigaichi, I. Shiina. Asian Journal of Organic Chemistry.2013, 2, 920–922. https://doi.org/10.1002/ajoc.201300139 [Highlighted in ChemistryViews]

(32) Novel Tamoxifen Derivative Ridaifen-B Induces Bcl-2 Independent Autophagy without Estrogen Receptor Involvement. Y. Nagahara, M. Takeyoshi, S. Sakemoto, I. Shiina, K. Nakata, K. Fujimori, Y. Wang, E. Umeda, C. Watanabe, S. Uetake, T. Yamori, S. Dan, Y. Yoshimi, T. Shiomiya, M. Ikekita. Biochemical and Biophysical Research Communications.2013, 435, 657–663.

(31) Kinetic Resolution of Racemic 2-Hydroxy-γ-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst. K. Nakata, K. Gotoh, K. Ono, K. Futami, I. Shiina. Organic Letters.2013, 15, 1170–1173.

(30) Kinetic Resolution of Racemic Secondary Benzylic Alcohols by the Enantioselective Esterification of Using Pyridine-3-carboxylic Anhydride (3-PCA) with Chiral Acyl-Transfer Catalysts. I. Shiina, K. Nakata, K. Ono, T. Mukaiyama. Helvetica Chimica Acta.2012, 95, 1891–1911.

(29) A New Method for Production of Chiral 2-Aryloxypropanoic Acids Using Effective Kinetic Resolution of Racemic 2-Aryloxycarboxylic Acids. A. Tengeigi, K. Nakata, K. Ono, I. Shiina. Heterocycles.2012, 86, 1227–1252.

(28) Non-enzymatic Dynamic Kinetic Resolution of Racemic α-Arylalkanoic Acids: An Advanced Asymmetric Synthesis of Chiral Nonsteroidal Anti-inflammatory Drugs (NSAIDs). I. Shiina, K. Ono, K. Nakata. Catalysis – Science & Technology2012, 2, 2200–2205.

(27) A Convenient Method for the Kinetic Resolution of Racemic 2-Hydroxyalkanoates Using Diphenylacetic Anhydride (DPHAA) and a Cchiral Acyl-Transfer Catalyst. K. Nakata, A. Sekiguchi, I. Shiina. Tetrahedron: Asymmetry.2011, 22, 1610–1619.

(26) Synthesis of an Advanced Intermediate toward the hNK-1 Antagonist with the Cyclopentane Core. K. Nakata, Y. Kiyotsuka, T. Kitazume, Y. Kobayashi. Synlett.2011, 19, 2872–2874.

(25) (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) Catalyzed Kinetic Resolution of Racemic Secondary Benzylic Alcohols with Free Carboxylic Acids by Asymmetric Esterification. K. Nakata, I. Shiina. Organic & Biomolecular Chemistry.2011, 9, 7092–7096.

(24) Ridaifen-G Induced Caspase-independent Atypical Cell Death. A. Anlifeire, M. Hatori, A. Morita, I. Shiina, K. Nakata, Y. Tosaki, Y.-W. Wang, M. Ikekita, G. Li. Chinese Journal of Cell Biology.2011, 33, 635–644.

(23) Kinetic Resolution of the Racemic 1-(Aryloxazol-2-yl)carbinols with Achiral Carboxylic Acids by Asymmetric Esterification: A New Method for the Preparing Chiral 1,2-Amino Alcohols. K. Nakata, K. Ono, I. Shiina. Heterocycles.2011, 82, 1171–1180.

(22) Kintic Resolution of the Racemic 1-Heteroarylalkanols by the Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst. I. Shiina, K. Ono, K. Nakata. Chemistry Letters.2011, 40, 147–149.

(21) Synthesis of Lasofoxifen, Nafoxidine and Their Positional Isomers via the Novel Three-Component Coupling Reaction. K. Nakata, Y. Sano, I. Shiina. Molecules.2010, 15, 6773–6794.

(20) An Effective Kinetic Resolution of Racemic α-Arylpropanoic Acids, α-Arylbutanoic Acids, and β-Substituted-α-arylpropanoic Acids with Bis(9-phenanthryl)methanol as a New Achiral Nucleophile in the Asymmetric Esterification Using Carboxylic Anhydrides and the Acyl-transfer Catalyst. K. Nakata, Y. Onda, K. Ono, I. Shiina. Tetrahedron Letters.2010, 51, 5666–5669.

(19) Kinetic Resolution of Racemic α-Arylalkanoic Acids with Achral Alcohols via the Asymmetric Esterification Using Carboxylic Anhydrides and Acyl-Tansfer Catalysts. I. Shiina, K. Nakata, K. Ono, Y. Onda, M. Itagaki. Journal of the American Chemical Society.2010, 132, 11629–11641.

(18) Kinetic Resolution of the Racemic 2-Hydroxyalkanoates Using the Enantioselective Mixed-Anhydride Method with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst. I. Shiina, K. Nakata, K. Ono, M. Sugimoto, A. Sekiguchi. Chemistry – A European Journal.2010, 16, 167–172.

(17) An Effective Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using 3-Pyridinecarboxylic Anhydride and a Chiral Acyl-Transfer Catalyst in the Absence of Tertiary Amine. K. Nakata, I. Shiina. Heterocycles.2010, 80, 169–175.

(16) Allylic Substitution of 4-Cyclopentene-1,3-diol Monoacetate with Copper Reagents Derived from Functionalized Aryl Grignard Reagents. Y. Kobayashi, Y. Tani, K. Nakata, Y. Kaneko. Synlett.2010, 2, 325–328.

(15) 2,2-Disubstituted Propionic Anhydrides: Effective Coupling Reagents for the Kinetic Resolution of Secondary Benzylic Alcohols Using BTM. I. Shiina, K. Nakata, M. Sugimoto, Y. Onda, T. Iizumi, K. Ono. Heterocycles.2009, 77, 801–810.

(14) Kinetic Resolution of Racemic Carboxylic Acids Using Achiral Alcohols by the Promotion of Benzoic Anhydrides and Tetramisole Derivatives: An Application to Produce Chiral Nonsteroidal Anti-inflammatory Drugs and Their Esters. I. Shiina, K. Nakata, Y. Onda. European Journal of Organic Chemistry.2008, 2008, 5887–5890.

(13) Realization of Anti-SN2’ Selective Allylation of 4-Cyclopentene-1,3-diol Monoester with Aryl- and Alkenyl Zinc Reagents. K. Nakata, Y. Kiyotsuka, T. Kitazume, Y. Kobayashi. Organic Letters.2008, 10, 1345–1348.

(12) Induction of Mitochondria-Involved Apoptosis in Estrogen Receptor Negative Cells by a Novel Tamoxifen Derivative, Ridaifen B. Y. Nagahara, I. Shiina, K. Nakata, A. Sasaki, T. Miyamoto, M. Ikekita. Cancer Science.2008, 99, 608–614.

(11) Synthesis and Pharmacological Evaluation of the Novel pseudo-Symmetrical Tamoxifen Derivatives as Anti-tumor Agents. I. Shiina, Y. Sano, K. Nakata, T. Kikuchi, A. Saski, M. Ikekita, Y. Nagahara, Y. Hasome, T. Yamori, K. Yamazaki.Biochemical Pharmacology.2008, 75, 1014–1026.

(10) 4-(Dimethylamino)pyridine N-oxide (DMAPO): an Effective Nucleophilic Catalyst in the Peptide Coupling Reacion Using 2-Methyl-6-nitrobenzoic anhydride. I. Shiina, H. Ushiyama, Y. Yamada, Y. Kawakita, K. Nakata. Chemistry – An Asian Journal.2008, 3, 454–461. 

(9) An Expeditious Synthesis of Tamoxifen, A Representative SERM (Selective Estrogen Receptor Modulator), via the Three-Component Coupling Reaction among Aromatic Aldehyde, Cinnamyltrimethylsilane and β-Chlorophenetole. I. Shiina, Y. Sano, K. Nakata, M. Suzuki, T. Yokoyama, A. Sasaki, T. Orikasa, T. Miyamoto, M. Ikekita, Y. Nagahara, Y. Hasome. Bioorganic & Medicinal Chemistry.2007, 15, 7599–7617.

(8) The First Asymmetric Esterification of Free Carboxylic Acids with Racemic Alcohols Using Benzoic Anhydrides and Tetramisole Derivatives: An Application to the Kinetic Resolution of Secondary Benzylic Alcohols. I. Shiina, K. Nakata.Tetrahedron Letters.2007, 48, 8314–8317.

(7) Synthesis of the New pseudo-Symmetrical Tamoxifen Derivatives and Their Anti-tumor Activity. I. Shiina, Y. Sano, K. Nakata, T. Kikuchi, A. Sasaki, M. Ikekita, Y. Hasome. Bioorganic & Medicinal Chemistry Letters.2007, 17, 2421–2424.

(6) An Expeditious Synthesis of Lasofoxifene and Nafoxidine via the Novel Three-component Coupling Reaction. Y. Sano, K. Nakata, T. Otoyama, S. Umeda, I. Shiina. Chemistry Letters.2007, 36, 40–41.

(5) Aryl- and Alkenyllithium Preparations and Copper-Catalyzed Reaction between the Derived Magnesium Reagents and the Monoacetate of 4-Cyclopentene-1,3-diol. K. Nakata, Y. Kobayashi. Organic Letters.2005, 7, 1319–1322.

(4) New Reagent System for Attaining High Regio- and Stereoselectivities in Allylic Displacemet of 4-Cyclopentene-1,3-diol Monoacetate with Aryl- and Alkenylmagnesium Bromide. Y. Kobayashi, K. Nakata, T. Ainai. Organic Letters.2005, 2, 183–186.

(3) (Salen)ruthenium-Catalyzed Desymmetrization of Meso-Diols: Catalytic Aerobic Asymmetric Oxidation under Photo-Irradiation. H. Shimizu, K. Nakata, T. Katsuki. Chemistry Letters.2002, 1080–1081. 

(2) Synthesis and Reactivity of (1-Fluorovinyl)phenyl Sulfoxide as a Dienophile. T. Hanamto, K. Korekoda, K. Nakata, K. Hamada, Y. Koga, M. Kondo. Journal of Fluorine Chemistry.2002, 118, 99–101. 

(1) Asymmetric Epoxidation with a Photoactivated [Ru(salen)] Complex. K. Nakata, T. Takeda, J. Mihara, T. Hamada, R. Irie, T. Katsuki. Chemistry – A European Journal 2001, 7, 3776–3782.