論文 - 有光　暁

Primary Amine-Catalyzed Enantioselective Fluorination of α-Branched Aldehydes with Low Catalyst Loadings

Endo, K; Sakahara, S; Tomon, D; Genka, R; Sugiyama, K; Higashi, M; Arimitsu, S

JOURNAL OF ORGANIC CHEMISTRY ( Journal of Organic Chemistry )  90 ( 51 ) 18296 - 18301   2025年12月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Synthesis of Diverse β,β-Diaryl β-Siloxy Diamines and Application as Organocatalysts

Takahara, K; Endo, K; Tomon, D; Arimitsu, S

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY ( European Journal of Organic Chemistry )  28 ( 33 )   2025年09月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Recent Advances in Allylic Fluoride Synthesis

Tomon, D; Arimitsu, S

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY ( European Journal of Organic Chemistry )  28 ( 6 )   2025年02月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Redox-economical synthesis of α-substituted α-N-phthaloyl amino aldehydes using Fukuyama reduction

Genka, R; Arimitsu, S

TETRAHEDRON LETTERS ( Tetrahedron Letters )  137   2024年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Selective Fluorination of Multi-Substituted Aldehydes or Ketones Using Amino Catalysts

Arimitsu, S

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   82 ( 6 ) 581 - 593   2024年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Synthesis of Chiral Tertiary Allylic- and Propargylic Fluorides from Nonaflates of Chiral α-Fluorinated β-Keto Dicarbonyl Compounds

Tomon, D; Arimitsu, S

JOURNAL OF ORGANIC CHEMISTRY ( Journal of Organic Chemistry )  88 ( 16 ) 11895 - 11904   2023年07月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Quantitative Chemical Analysis of Defensive Secretion of Megacrania tsudai (Phasmatidae) and Effect of Actinidine on its Potential Predators.

Kobayashi S, Arimitsu S, Takaoka C, Ono T, Izawa M

Journal of chemical ecology ( Journal of Chemical Ecology )  49 ( 9-10 ) 537 - 548   2023年06月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Alkali Carbonates Improve β,β-Diaryl Serine-Catalyzed Enantioselective α-Fluorination of β-Dicarbonyl Compounds.

Endo K, Tomon D, Arimitsu S

The Journal of organic chemistry ( Journal of Organic Chemistry )  88 ( 13 ) 9037 - 9045   2023年05月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Syntheses and Synthetic Applications of Functionalized Propargylic and Allylic Fluorides.

Arimitsu S

Chemical record (New York, N.Y.) ( Chemical Record )  23 ( 9 ) e202300021   2023年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Diastereoselective synthesis of γ,γ-disubstituted β-hydroxy α,α-difluoro-γ-butyrolactones

Ishikawa T.

Journal of Fluorine Chemistry ( Journal of Fluorine Chemistry )  261-262   2022年09月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Effect of spraying behavior and body size on predators of the big head stick insect Megacrania tsudai (Phasmatodea: Phasmatidae)

Kobayashi S.

Entomological Science ( Entomological Science )  25 ( 2 )   2022年06月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Enantioselective Fluorination of α-Substituted β-Diketones Using β,β-Diaryl Serines.

Poorsadeghi S, Endo K, Arimitsu S

Organic letters ( Organic Letters )  24 ( 1 ) 420 - 424   2022年01月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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One-pot synthesis of new alkyl 1-naphthoates bearing quinoline, pyranone and cyclohexenone moieties via metal-free sequential addition/oxidation reactions.

Mousavi SH, Mohammadizadeh MR, Poorsadeghi S, Arimitsu S, Mohammadsaleh F, Kojya G, Gima S

RSC advances ( RSC Advances )  11 ( 58 ) 36748 - 36752   2021年11月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Enantioselective Fluorination of α-Branched β-Ynone Esters Using a Cinchona-Based Phase-Transfer Catalyst.

Arimitsu S, Iwasa S, Arakaki R

The Journal of organic chemistry ( Journal of Organic Chemistry )  85 ( 19 ) 12804 - 12812   2020年10月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Herein, we report the fluorination of α-branched β-ynone esters to afford their corresponding quaternary fluorinated products with good enantioselectivity (ee = 73-90%) using a cinchona-based phase-transfer catalyst. α-Branched β-ynone esters possess a highly acidic α-proton and form their corresponding enolate as a single isomer, which allows the enantioselective fluorination reaction to occur under standard cinchona-based phase-transfer catalyst conditions. Moreover, the obtained α-fluorinated product can be treated with [(SPhos)AuNTf2] (1 mol %) to afford a fluorinated 3,5-diketo carboxylic acid.

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One-Pot Synthesis of Spiro-isobenzofuran Compounds <i>via</i> the Sequential Condensation/Oxidation Reaction of Ninhydrin with 4-Amino-1,2-naphthoquinones/2-Amino-1,4-naphthoquinones under Mild Conditions.

Mousavi SH, Mohammadizadeh MR, Roshan Z, Jamaleddini A, Arimitsu S

ACS omega ( AMER CHEMICAL SOC )  5 ( 29 ) 18273 - 18288   2020年07月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Copyright © 2020 American Chemical Society. A one-pot route for the synthesis of spiro-isobenzofuran compounds was developed via the condensation reaction of ninhydrin with 4-amino-1,2-naphthoquinones or 2-amino-1,4-naphthoquinones in acetic acid followed by the oxidative cleavage of the corresponding vicinal diols at room temperature. Various derivatives of spiro[benzo[g]indole-2,1′-isobenzofuran]-3,3′,4,5(1H) tetraones and spiro[benzo[f]pyrrolo[2,3-h]quinoxaline-2,1′-isobenzofuran]-3,3′(1H)-diones were synthesized in good to high yields. Moreover, further condensation of spiro[benzo[g]indole-2,1′-isobenzofuran]-3,3′,4,5(1H)-tetraones with 1,2-diamines resulted in the new spiro-isobenzofuran compounds having phenazine rings in high yields.

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Improvement of primary-amine-catalyzed asymmetric α-benzoyloxylation of α-branched enals by a synergistic effect of water and sulfonic acids

Satoru Arimitsu, Emi Gima

Tetrahedron Letters ( Tetrahedron Letters )  61 ( 25 )   2020年06月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2020 Elsevier Ltd The asymmetric α-benzoyloxylation of α-branched enals developed by List was reinvestigated to further improve its reaction efficiency and enantioselectivity. After optimizing the reaction conditions, the synergistic effect of water and sulfonic acid in DMSO was revealed. The reaction efficiency was improved reducing the reaction time, and moderate enantioselectivities (up to 81% ee) with excellent E selectivity (E/Z = >20/1) were achieved. Although regioselectivity was not as high (α/γ = 1/1–6/1), α-regioisomer 2a was successfully applied to synthesize high stereo-control compounds consisting of an oxygenated quaternary carbon with two allylic units (E/Z = 20/1, 20/1).

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Metal-free syntheses of new azocinesviaaddition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols

S. Hekmat Mousavi, Mohammad Reza Mohammadizadeh, Satoru Arimitsu, Dariush Saberi, Samira Poorsadeghi, Kojya Genta

RSC Advances ( ROYAL SOC CHEMISTRY )  10 ( 35 ) 20552 - 20557   2020年05月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© The Royal Society of Chemistry 2020. A one-pot, clean and green procedure is described for the syntheses of new azocine derivativesviaaddition reactions of enaminones with acenaphthoquinone followed by periodic acid-mediated oxidative cleavages of the corresponding vicinal diols. Various derivatives of azocine were prepared and well characterized. The excellent yields, simple synthesis procedure, lack of a need to carry out any tedious work-up and column chromatography, metal-free catalysis, and mild reaction conditions are important features of this protocol.

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Preparation of Enantiomerically Pure β,β-Diaryl β-Hydroxy-α-Amino Acids and Evaluation of Their Potential as Organocatalysts

Satoru Arimitsu, Koki Oshiro, Katsuki Endo, Emi Gima, Samira Poorsadeghi

Asian Journal of Organic Chemistry ( Asian Journal of Organic Chemistry )  9 ( 2 ) 238 - 241   2020年02月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A general synthetic procedure was developed for enantiomerically pure β,β-diaryl β-hydroxy-α-amino acids 5, starting from readily available oxazolidine ester 1 and a wide variety of Grignard reagents. The problematic oxidative decomposition of β-aminodiols 3, due to their instability in the presence of metallic oxidants, was successfully suppressed using Parikh-Doering oxidation and subsequent Pinnick oxidation. Additionally, the organocatalytic ability of β,β-diaryl β-hydroxy-α-amino acids 5 was evaluated with respect to asymmetric fluorination of 2-phenylpropionaldehyde 6, and moderate enantioselectivity, 61%, was achieved using compound 5 f.

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Effects of Water Addition on a Catalytic Fluorination of Dienamine.

Kuraoku D, Yonamine T, Koja G, Yoshida N, Arimitsu S, Higashi M

Molecules (Basel, Switzerland) ( Molecules )  24 ( 19 )   2019年09月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2019 by the authors. We investigate the effects of water addition on a highly stereocontrolled fluorination of dienamine generated by α-branched enals and 60-hydroxy-9-amino-9-deoxy-epi-quinidine with N-fluorobenzenesulfonimide (NFSI) in the presence of Brønsted acid both experimentally and theoretically. It is experimentally found that water addition to organic solvent significantly shortens the reaction time whereas excessive water addition decreases the enantiomeric excess. The results calculated with three-dimensional reference interaction site model self-consistent field (3D-RISM-SCF) method are in good agreement with the experimental ones. It is revealed that the shortness of reaction time is caused by the reactant destabilization and that the decrease in enantiomeric excess is due to the difference of hydration free energy between two transition states.

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CHAPTER 2: Importance of C-H hydrogen bonding in asymmetric catalysis

Satoru Arimitsu, Masahiro Higashi

RSC Catalysis Series ( RSC Catalysis Series )  2019-January ( 37 ) 26 - 65   2019年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2019 The Royal Society of Chemistry. This chapter describes the important roles of nonclassical C-H hydrogen bonds in asymmetric catalysis. Recently, many asymmetric catalytic reactions have demonstrated that weak C-H hydrogen bond interactions play important roles in selectivity. This chapter introduces the historical background of C-H hydrogen bonds, describes computational analyses of C-H hydrogen bonds in asymmetric catalysis and presents notable examples of asymmetric catalytic reactions in which C-H hydrogen bonds play important roles in selectivity.

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