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 ]

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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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Importance of C-H Hydrogen Bonding in Asymmetric Catalysis

Arimitsu, S; Higashi, M

NONCOVALENT INTERACTIONS IN CATALYSIS   36   26 - 65   2019年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

Diastereoselective synthesis of 5,5-disubstituted 3,3-difluorotetrahydrofurans

Satoru Arimitsu, Makoto Nakasone, Emi Gima

Tetrahedron Letters ( Elsevier Ltd )  59 ( 10 ) 887 - 890   2018年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2018 Elsevier Ltd The diastereoselective synthesis of 5,5-disubstituted 3,3-difluorotetrahydrofurans 2 was achieved using β,β-difluorohomoallylic alcohols 1 as the key starting material in the presence of ICl (3.0 equiv) and tert-BuOK (1.5 equiv) in THF. The corresponding iodocyclization products 2 were obtained in good to moderate yields with excellent diastereo- and regioselectivities (d.r. = >20/1, 5-endo-trig only).

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Stereoselective Synthesis of 4-Substituted 2,4-Dichloro-2-butenals by α- And γ-Regioselective Double Chlorination of Dienamine Catalysis

Satoru Arimitsu, Kazuto Terukina, Tatsuro Ishikawa

Synlett ( Synlett )  29 ( 14 ) 1887 - 1891   2018年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© Georg Thieme Verlag Stuttgart New York. The L-proline-catalyzed reaction of enolizable α,β-unsaturated aldehydes with N-chlorosuccinimide (NCS) gave the corresponding 4-substituted 2,4-dichloro-2-butenals with moderate yields and excellent diastereoselectivities (Z / E = >20/1) through consecutive double chlorination at the α- and γ-positions of the dienamine intermediate. The corresponding 2,4-dichloro-2-butenals contain a multireactive 1,3-dichloro allylic unit useful for the construction of Z -vinyl chlorides; the chloride on the allylic position was replaced with mild nucleophiles such as MeOH and EtOH via an S N 2 substitution reaction, and its aldehyde moiety was used as a synthetic handle and transformed into an alcohol or a vinyl group. All products obtained after those synthetic manipulations maintained excellent diastereoselectivities (Z/E = >20/1).

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Cinchona-Based Primary Amine Catalyzed a Proximal Functionalization of Dienamines: Asymmetric α-Fluorination of α-Branched Enals

Satoru Arimitsu, Tsunaki Yonamine, Masahiro Higashi

ACS Catalysis ( AMER CHEMICAL SOC )  7 ( 7 ) 4736 - 4740   2017年07月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2017 American Chemical Society. Fluorination of dienamines generated by α-branched enals and 6′-hydroxy-9-amino-9-deoxy-epi-quinidine (30 mol %) with NSFI show excellent α-regioselectivity to construct allylic fluorides containing a highly stereocontrolled quaternary fluorinated carbon (E/Z ≥ 20/1 and up to 93% enantiometric excess (ee)). By DFT calculation, the quinuclidine moiety of the catalyst was shown to function as a coordinating group to promote a reaction at the proximal α-position, and the nonclassical CH hydrogen bond plays an important role in the high enantioselectivity.

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A new umpolung for direct γ-regioselective nucleophilic addition of alcohols to γ-enolizable α,β-unsaturated aldehydes

Satoru Arimitsu, Mari Oshiro, Tsunaki Yonamine

Tetrahedron Letters ( PERGAMON-ELSEVIER SCIENCE LTD )  58 ( 25 ) 2517 - 2520   2017年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2017 Elsevier Ltd A direct γ-regioselective nucleophilic addition of alcohols toward γ-enolizable α,β-unsaturated aldehydes was developed using a catalytic amount of MeSO3H (30 mol%) and a stoichiometric amount of chloranil (1.0 equiv) as the oxidant. The addition of hexafluoroisopropanol (HFIP) was found to accelerate this cross-dehydrogenative coupling, furnishing diverse alcoholic adducts with high γ-regio- and E-stereoselectivities.

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Stereoselective Organocatalytic Synthesis of α,α-Difluoro-γ,γ-Disubstituted Butenals.

Arimitsu S, Nakasone M

The Journal of organic chemistry ( AMER CHEMICAL SOC )  81 ( 15 ) 6707 - 13   2016年08月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 American Chemical Society. A highly stereoselective reaction of α,α-difluoro-γ,γ-disubstituted butenals 2 bearing two different substituents at the γ position has been developed with an organocatalytic system of l-proline (30 mol %) and salicylic acid (60 mol %). This novel reaction demonstrated a wide substrate scope and excellent E stereoselectivity in most cases. The obtained difluorinated aldehyde 2a was applied as a useful synthetic precursor for constructing 3,3-disubstituted allylic difluoride moieties.

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Highly Stereoselective Synthesis of Fluoroalkene Dipeptides via the Novel Chromium(II)-Mediated Carbon-Fluorine Bond Cleavage/New Carbon-Carbon Bond Formation

Takashi Nihei, Yuji Nishi, Natsumi Ikeda, Saya Yokotani, Takashi Ishihara, Satoru Arimitsu, Tsutomu Konno

Synthesis (Germany) ( GEORG THIEME VERLAG KG )  48 ( 6 ) 865 - 881   2016年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 Georg Thieme Verlag Stuttgart. New York. An efficient chromium(II)-mediated reductive coupling reaction of various CBrF2-containing molecules and aldehydes has been developed. This reaction proceeds presumably via the monofluorinated dichromium(III) intermediate generated by the carbon-fluorine bond activation, and provides a general and straightforward access to synthesize a variety of (E)- or (Z)-β-fluoroallylic alcohols in a highly stereoselective manner. Based on the novel reductive coupling, four types of fluoroalkene dipeptide analogues could be stereoselectively prepared.

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One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides

Yoshiki Toma, Masataka Kunigami, K. jiro Watanabe, Masahiro Higashi, Satoru Arimitsu

Journal of Fluorine Chemistry ( ELSEVIER SCIENCE SA )  189   22 - 32   2016年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 Elsevier B.V. The reaction with β-trifluoromethyl acrylamide 3e and azomethine ylides generated from L-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities.

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Application of Tertiary Amines Synthesized by Catalytic Dehydrogenation of Enamines as Nucleophilic C₂ Synthons for 1,4-Conjugate Addition with Fluoroalkylated Olefins

Morigaki, A; Kawamura, M; Arimitsu, S; Ishihara, T; Konno, T

ASIAN JOURNAL OF ORGANIC CHEMISTRY   2 ( 3 ) 239 - 243   2013年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Unusual annulation reaction of electron-deficient alkenes with enamines: an easy access to stereocontrolled 4-fluoroalkylated 3,4-dihydro-2<i>H</i>-pyrans

Morigaki, A; Tsukade, K; Arimitsu, S; Konno, T; Kubota, T

TETRAHEDRON   69 ( 5 ) 1521 - 1525   2013年02月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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The First Practical Additive-Free 1,4-Conjugated Alkylation of Fluoro-alkylated Electron-Deficient Olefins with Various Organozinc Reagents

Morigaki, A; Miyabe, T; Tsukade, K; Arimitsu, S; Ishihara, T; Konno, T

SYNTHESIS-STUTTGART   45 ( 1 ) 101 - 105   2013年01月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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An Achiral-Acid-Induced Switch in the Enantioselectivity of a Chiral cis-Diamine-Based Organocatalyst for Asymmetric Aldol and Mannich Reactions†

Dr. Shin A. Moteki, Jianwei Han, Satoru Arimitsu, Dr. Matsujiro Akakura, Keiji Nakayama and Prof. Dr. Keiji Maruoka1,*

ACIE ( その他の出版社 )  51 ( 5 ) 1187   2012年

掲載種別: 研究論文（その他学術会議資料等）

Design of Structurally Rigid trans-Diamine-Based Tf-Amide Organocatalysts with a Dihydroanthracene Framework for Asymmetric Conjugate Additions of Heterosubstituted Aldehydes to Vinyl Sulfones

Shin A. Moteki , Senmiao Xu , Satoru Arimitsu , and Keiji Maruoka *

JACS ( その他の出版社 )  132 ( 48 ) 17074   2010年

掲載種別: 研究論文（その他学術会議資料等）

Synthesis of 2, 4, 5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols

Satoru Arimitsu , Jesse M. Jacobsen , and Gerald B. Hammond *

JOC ( その他の出版社 )  73 ( 7 ) 2886   2008年

掲載種別: 研究論文（その他学術会議資料等）

Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

Santos Fustero, Begoña Fernández, Paula Bello, Carlos del Pozo, Satoru Arimitsu, and Gerald B. Hammond

OL ( その他の出版社 )  9 ( 21 ) 4251   2007年

掲載種別: 研究論文（その他学術会議資料等）