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原著論文

(65) A Facile Preparation of Tetrasubstituted Arylalkenes Catalyzed by p-Toluenesulfonic Acid Monohydrate (p-TsOH·H2O): Application in the Synthesis of the Intermediate of TamoxifenT. Sutani, N. Kimura, K. NakataChemistrySelect 2024, 9, e20240295. 

https://doi.org/10.1002/slct.202402951

(64) Enantioselecyive Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines. A. Ui, M. Iwakura, S. Yoshimatsu, K. NakataSynlett 2024, in press. 

https://doi.org/10.1055/a-2322-0904

(63) Acylative and Silylative Dynamic Kinetic Resolutions of 6-Hydroxy-2H-pyran-3(6H)-one Catalyzed by Chiral Guanidines. K. Miyazaki, K. NakataSynlett 2024, 35, 1591–1595. 

https://doi.org/10.1055/a-2206-7545

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(62) Diastereoselective Cross-Dehydrogenative Coupling Reactions of Amides with Diarylmethanes Using DDQ through C–H Benzylic Activation. N. Kimura, K. NakataSynlett 2024, 35, 240–244. 

https://doi.org/10.1055/a-2182-7532

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(61) Design and Synthesis of Axial-Chirality-Containing Guanidine Catalysts. M. Iwakura, T. Ikeue, K. NakataChemistrySelect 2022, 7, e202202511. 

https://doi.org/10.1002/slct.202202511

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(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. NakataThe Journal of Organic Chemistry 2022, 87, 10509–10515. 

https://doi.org/10.1021/acs.joc.2c01129

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(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

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(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

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(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

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(56) Lewis Acid-Catalyzed Nucleophilic Substitutions of Benzylic Alcohols with Sulfamides. R. Oda, K. Nakata. European Journal of Organic Chemistry 2021, 295–301. 

https://doi.org/10.1002/ejoc.202001320

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(55) Chemodiergent Dehydrative Nucleophilic Substitutions of Diarylmethanols with 1-Phenyl-1H-tetrazole-5-thiol Catalyzed by FeCl3R. Oda, K. Nakata. Asian Journal of Organic Chemistry 2020, 9, 1234–1242. 

https://doi.org/10.1002/ajoc.202000301

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(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

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(53) Diastereoconvergent Dehydrative Nucleophilic Substitutions of Diastereomeric Diarylmethanols with 1,3-Dicarbonyls Catalyzed by SnBr4R. Kubo, H. Yamamoto, K. Nakata. European Journal of Organic Chemistry 2019, 7394–7398. 

https://doi.org/10.1002/ejoc.201901377

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(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

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(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.201803162

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(50) Diastereoconergent Synthesis of Chiral Diarylmethyl Sulfones by Direct Sulfonylation of Diarylmethanols Diastereomixtures with Sodium Sulfinates Catalyzed by SnBr2H. Yamamoto, K. Nakata. European Journal of Organic Chemistry 2019, 4906–4910. 

https://doi.org/10.1002/ejoc.201900830

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(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

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(47) Chiral-Auxiliary-Controlled Diastereoconvergent Benzamidation Reactions of Diastereomixtures of Diarylmethanols with Benzamide Catalyzed by SnBr4R. Kubo, K. Nakata. Asian Journal of Organic Chemistry 2019, 8, 119–122. 

https://doi.org/10.1002/ajoc.201800635

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(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

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(45) Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3R. Fujihara, K. Nakata. European Journal of Organic Chemistry 2018, 6566–6573. 

https://doi.org/10.1002/ejoc.201801236

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(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

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(42) Chiral Inductive Diastereoconvergent Friedel–Crafts Alkylation Reaction of Diastereomixtures of Diarylmethanols with 2-Naphthol Derivatives Catalyzed by SnBr4N. Suzuki, K. Nakata. European Journal of Organic Chemistry 2017, 7075–7086. 

https://doi.org/10.1002/ejoc.201701280

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(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

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(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

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(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

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(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

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(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

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(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]

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(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 & Technology 2012, 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, 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.

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