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Department of Material Chemistry, Graduate School of Engineering

Kyoto University, Japan

京都大学大学院 工学研究科 材料化学専攻

The Matsubara Group

松原研究室

Laboratory of organic reaction chemistry

有機反応化学分野

Publications

2022

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Non-Enzymatic Catalytic Asymmetric Cyanation of Acylsilanes
Nagano, T.; Matsumoto, A.; Yoshizaki, R.; Asano, K.; Matsubara, S.
Commun. Chem. 2022, 5, 45.

Commun. Chem. 2022_Nagano.png

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データ駆動で有機分子をつくれるか？
Matsubara, S.
現代化学 2022, 612.

2021

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Catalytic Asymmetric Cycloetherification via Intramolecular Oxy-Michael Addition of Enols
Murata, R.; Asano, K.; Matsubara, S.
Tetrahedron 2021, 97, 132381.

Tetrahedron 2021_Murata.png

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Unmasking Inherent Chirality within the Cubane Skeleton
Yoshino, N.; Kato, Y.; Shimada, Y.; Williams, C. M.; Matsubara, S.
Isr. J. Chem. 2021, 61, 380–386.

Isr. J. Chem. 2021_Yoshino.jpg

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Digitization of Organic Synthesis ---- How Synthetic Organic Chemists Use AI Technology ----
Matsubara, S.
Chem. Lett. 2021, 50, 475–481.
Selected as the backcover.

Chem. Lett. 2021_Matsubara.gif
Chem. Lett. 2021_Matsubara_Backcover.jpg

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Multipoint Recognition of Molecular Conformations with Organocatalysts for Asymmetric Synthetic Reactions
Asano, K.
Bull. Chem. Soc. Jpn. 2021, 94, 694–712.
Selected as the inside cover.

Bull. Chem. Soc. Jpn. 2020_Asano.png
Bull. Chem. Soc. Jpn. 2021_Asano_Inside

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Preparation of 2-Aryl-3-silyl- and 2-Aryl-3-germyl-1,3-butadienes via Arylnickelation and Zinciomethylation
Yoshino, N.; Sharewa, B.; Ikeda, Z.; Matsubara, S.
Heterocycles 2021, 103, 769–777.

Heterocycles 2020_Yoshino.png

2020

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有機合成のデジタル化

Matsubara, S.

日本化学会情報化学部会誌 2020, 38, 8–11.

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Desymmetrization of gem-Diols via Water-Assisted Organocatalytic Enantio- and Diastereoselective Cycloetherification

Murata, R.; Matsumoto, A.; Asano, K.; Matsubara, S.

Chem. Commun. 2020, 56, 12335–12338.

Selected as the inside back cover.

Highlighted in Synfacts 2020, 16, 1276.

Chem. Commun. 2020_Murata.png
Chem. Commun. 2020_Murata_inside back co

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trans‐Cyclooctenes as Chiral Ligands in Rhodium-Catalyzed Asymmetric 1,4-Additions

Nagano, T.; Einaru, S.; Shitamichi, K.; Asano, K.; Matsubara, S.

Eur. J. Org. Chem. 2020, 7131–7133.

Selected as the Very Important Paper (VIP).

Selected as the Front Cover.

Highlighted in ChemistryViews.

Eur. J. Org. Chem. 2020_Nagano.png
Eur. J. Org. Chem. 2020_Nagano_Front Cov

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Enantio- and Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis

Wada, Y.; Murata, R.; Fujii, Y.; Asano, K.; Matsubara, S.

Org. Lett. 2020, 22, 4710–4715.

Highlighted in Organic Chemistry Highlights in Organic Chemistry Portal.

Org. Lett. 2020_Wada.png

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Cubane Chirality via Substitution of a “Hidden” Regular Tetrahedron

Yoshino, N.; Kato, Y.; Mabit, T.; Nagata, Y.; Williams, C. M.; Harada, M.; Muranaka, A.;

Uchiyama, M.; Matsubara, S.

Org. Lett. 2020, 22, 4083–4087.

Org. Lett. 2020_Yoshino.jpg

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Nickel-Catalyzed Intermolecular Carbobromination of Alkynes

Takahashi, T.; Kurahashi, T.; Matsubara, S.

ACS Catal. 2020, 10, 3773–3777.

ACS Catal. 2020_Takahashi.gif

2019

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Enantioselective Bromination of Axially Chiral Cyanoarenes in the Presence of Bifunctional Organocatalysts

Wada, Y.; Matsumoto, A.; Asano, K.; Matsubara, S.

RSC Adv. 2019, 9, 31654–31658.

RSC Adv. 2019, 9, 31654.png

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Nickel-Catalyzed [5+2] Cycloaddition of 10π-Electron Aromatic Benzothiophenes with Alkynes To Form Thermally Metastable 12π-Electron Nonaromatic Benzothiepines

Inami, T.; Takahashi, T.; Kurahashi, T.; Matsubara, S.

J. Am. Chem. Soc. 2019, 141, 12541–12544.

J. Am. Chem. Soc. 2019, ASAP (Inami).gif

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Chlorotrifluoromethylation of Terminal Olefins by Atom Transfer‐Type Radical Reaction Catalyzed by Cobalt Complexes

Maeda, K.; Kurahashi, T.; Matsubara, S.

Eur. J. Org. Chem. 2019, 4613–4616.

Eur. J. Org. Chem. 2019, 4613.jpg

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Asymmetric Aza‐Diels–Alder Reaction with Ion‐Paired – Iron Lewis Acid – Brønsted Acid Catalyst

Tomifuji, R.; Kurahashi, T.; Matsubara, S.

Chem.—Eur. J. 2019, 25, 8987–8991.

Selected as the top 10% most downloaded paper.

Chem. Eur. J. 2019, Accepted Article (To

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Cationic Cobalt Porphyrin-Catalyzed Allylation of Aldehydes with Allyltrimethylsilanes

Tomifuji, R.; Masuda, S.; Kurahashi, T.; Matsubara, S.

Org. Lett. 2019, 21, 3834–3837.

Org. Lett. 2019, ASAP (Tomifuji).gif

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Asymmetric syn-1,3-Dioxane Construction via Kinetic Resolution of Secondary Alcohols Using Chiral Phosphoric Acid Catalysts

Matsumoto, A.; Asano, K.; Matsubara, S.

Asian J. Org. Chem. 2019, 8, 814–818.

Asian J. Org. Chem. 2019, Accepted Artic

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Diastereoselective Synthesis of 1,3-Oxazolidines via Cationic Iron Porphyrin-catalyzed Cycloaddition of Aziridines with Aldehydes

Teranishi, S.; Maeda, K.; Kurahashi, T.; Matsubara, S.

Org. Lett. 2019, 21, 2593–2596.

Org. Lett. 2019, ASAP (Teranishi).gif

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Organocatalytic Enantio- and Diastereoselective Construction of syn-1,3-Diol Motifs via Dynamic Kinetic Resolution of In Situ Generated Chiral Cyanohydrins

Matsumoto, A.; Asano, K.; Matsubara, S.

Org. Lett. 2019, 21, 2688–2692.

Org. Lett. 2019, ASAP (Matsumoto).png

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Asymmetric Cycloetherification of in Situ Generated Cyanohydrins through the Concomitant Construction of Three Chiral Carbon Centers

Kurimoto, Y.; Nasu, T.; Fujii, Y.; Asano, K.; Matsubara, S.

Org. Lett. 2019, 21, 2156–2160.

Org. Lett. 2019, ASAP (Kurimoto).png

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反応集積化と中分子合成――新しい合成手法の開発

Matsubara, S.

化学と工業 2019, 72, 121–123.

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A Protocol for an Iodine–Metal Exchange Reaction on Cubane Using Lithium Organozincates

Kato, Y.; Williams, C. M.; Uchiyama, M.; Matsubara, S.

Org. Lett. 2019, 21, 473–475.

Org. Lett. 2019, ASAP (Kato).gif

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Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification

Matsumoto, A.; Asano, K.; Matsubara, S.

Chem.—Asian J. 2019, 14, 116–120.

Selected as the Cover Feature.

Selected as the top 10% most downloaded paper.

Chem. Asian J. 2018, Accepted Article (M
Chem. Asian J. 2019, (Matsumoto)_Cover P

2018

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H/D Exchange Using Hot Heavy Water

Matsubara, S.; Ishibashi, K.; Maung, G. Y. T.; Morota, Y.; Umemura, T.; Kato, Y.

Chimia 2018, 72, 853–858.

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FeCl3 as an Ion-Pairing Lewis Acid Catalyst. Formation of Highly Lewis Acidic FeCl2+ and Thermodynamically Stable FeCl4– To Catalyze the Aza-Diels–Alder Reaction with High Turnover Frequency

Tomifuji, R.; Maeda, K.; Takahashi, T.; Kurahashi, T.; Matsubara, S.

Org. Lett. 2018, 20, 7474–7477.

Org. Lett. 2018, ASAP (Tomifuji).gif

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Nickel-catalyzed Intermolecular Carboiodination of Alkynes with Aryl Iodides

Takahashi, T.; Kuroda, D.; Kuwano, T.; Yoshida, Y.; Kurahashi, T.; Matsubara, S.

Chem. Commun. 2018, 54, 12750–12753.

Chem. Commun. 2018, Advance Article (Tak

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コンピュータ支援有機合成の現在

Matsubara, S.; Terayama, K.; Okuno, Y.

MEDCHEM NEWS 2018, 28 (4), 181–186.

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trans‐Cyclooctenes as Halolactonization Catalysts

Einaru, S.; Shitamichi, K.; Nagano, T.; Matsumoto, A.; Asano, K.; Matsubara, S.

Angew. Chem., Int. Ed. 2018, 57, 13863–13867.

Highlighted in Synfacts 2018, 14, 1198.

Angew. Chem., Int. Ed. 2018, 57, 13863.p

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Asymmetric Cycloetherification by Bifunctional Organocatalyst

Asano, K.; Matsubara, S.

Synthesis 2018, 50, 4243–4253.

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Catalytic Approaches to Optically Active 1,5-Benzothiazepines

Asano, K.; Matsubara, S.

ACS Catal. 2018, 8, 6273–6282.

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Chematicaは有機合成に新たな道を拓くのか？—AIと化学の未来像を探る

Matsubara, S.

化学 2018, 73 (6), 12–18.

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Ligand-controlled Behavior of Ag(I)–π Complex as σ-Lewis Acid

Maeda, K.; Takahashi, T.; Tomifuji, R.; Hirao, N.; Kurahashi, T.; Matsubara, S.

Chem. Lett. 2018, 47, 532–535.

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Molecular Transformations Using Bis(iodozincio)methane­–The Role of Chelation in Main Group Organometallic Chemistry

Matsubara, S.

Bull. Chem. Soc. Jpn. 2018, 91, 82–86.

BCSJ Account/Review Collection.

2017

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反応溶液の中身を見ようとした話 ～有機反応における「均一溶液」について～

Matsubara, S.

化学と工業 2017, 70, 1110–1112.

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Organocatalytic Enantio- and Diastereoselective Cycloetherification via Dynamic Kinetic Resolution of Chiral Cyanohydrins

Yoneda, N.; Fujii, Y.; Matsumoto, A.; Asano, K.; Matsubara, S.

Nat. Commun. 2017, 8, 1397.

Press release on Kyoto University website.

Highlighted in Newspapers (Nikkei Shinbun & Kagaku Kogyo Nippo).

Highlighted in Synform 2018, 3, A33.

Highlighted in Organic Chemistry Highlights in Organic Chemistry Portal.

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Asymmetric Net Cycloaddition for Access to Diverse Substituted 1,5-Benzothiazepines

Fukata, Y.; Yao, K.; Miyaji, R.; Asano, K.; Matsubara, S.

J. Org. Chem. 2017, 82, 12655–12668.

Highlighted in Abstracts in Organic Chemistry Portal.

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Bifunctional Organocatalysts for the Asymmetric Synthesis of Axially Chiral Benzamides

Miyaji, R.; Wada, Y.; Matsumoto, A.; Asano, K.; Matsubara, S.

Beilstein J. Org. Chem. 2017, 13, 1518–1523.

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Preparation of Organozinc Reagents via Catalyst Controlled Three-Component Coupling between Alkyne, Iodoarene, and Bis(iodozincio)methane

Shimada, Y.; Ikeda, Z.; Matsubara, S.

Org. Lett. 2017, 19, 3335–3337.

Highlighted in Synfacts 2017, 13, 973.

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Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts

Miyaji, R.; Asano, K.; Matsubara, S.

Chem.—Eur. J. 2017, 23, 9996–10000.

Selected as the Inside Cover.

Chem.—Eur. J. 2017, in press_

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“Naked” Lithium Cation: Strongly Activated Metal Cations Facilitated by Carborane Anions

Kitazawa, Y.; Takita, R.; Yoshida, K.; Muranaka, A.; Matsubara, S.; Uchiyama, M.

J. Org. Chem. 2017, 82, 1931–1935.

2016

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穏和な有機触媒がもたらす精密不斉合成

Asano, K.

有機合成化学協会誌 2016, 74, 1194–1205.

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Asymmetric Cycloetherification via the Kinetic Resolution of Alcohols Using Chiral Phosphoric Acid Catalysts

Yoneda, N.; Matsumoto, A.; Asano, K.; Matsubara, S.

Chem. Lett. 2016, 45, 1300–1303.

2015

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Asymmetric Synthesis of Spiroketals with Aminothiourea Catalysts

Yoneda, N.; Fukata, Y.; Asano, K.; Matsubara, S.

Angew. Chem., Int. Ed. 2015, 54, 15497–15500.

Highlighted in Synfacts 2016, 12, 89.

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Ruthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines

and Aldehydes

Maeda, K.; Terada, T.; Iwamoto, T.; Kurahashi, T.; Matsubara, S.

Org. Lett. 2015, 17, 5284–5287.

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Chemo- and Regioselective Preparation of Zinc Enolate from Thiol Esters by Palladium Catalyzed Cross-coupling Reaction

Haraguchi, R.; Ikeda, Z.; Ooguri, A.; Matsubara, S.

Tetrahedron 2015, 71, 8830–8837.

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穏やかな触媒がもたらす精密有機合成

Asano, K.

化学と工業 2015, 68, 832–833.

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Preparation of an Arenylmethylzinc Reagent with Functional Groups by Chemoselective Cross-Coupling Reaction of Bis(iodo­zincio)methane with Iodoarenes

Shimada, Y.; Haraguchi, R.; Matsubara, S.

Synlett 2015, 26, 2395–2398.

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Diastereoselective Reduction of β-(1,3-Dioxan-4-yl)ketones

Matsumoto, A.; Asano, K.; Matsubara, S.

Synlett 2015, 26, 1872–1874.

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A Chiral Phosphoric Acid Catalyst for Asymmetric Construction of 1,3-Dioxanes

Matsumoto, A.; Asano, K.; Matsubara, S.

Chem. Commun. 2015, 51, 11693–11696.

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A Triphenylamine with Two Phenoxy Radicals Having Unusual Bonding Patterns and a Closed-Shell Electronic State

Sakamaki, D.; Yano, S.; Kobashi, T.; Seki, S.; Kurahashi, T.; Matsubara, S.; Ito, A.; Tanaka, K.

Angew. Chem., Int. Ed. 2015, 54, 8267–8270.

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Nickel-catalyzed Reactions Directed toward the Formation of Heterocycles

Kurahashi, T.; Matsubara, S.

Acc. Chem. Res. 2015, 48, 1703–1716.

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フロー·マイクロリアクターを用いた有機亜鉛反応剤の反応—メチレン化から自己不斉増幅反応まで—

Matsubara, S.

有機合成化学協会誌 2015, 73, 435–441.

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Bifunctional Organocatalysts for the Enantioselective Synthesis of Axially Chiral Isoquinoline N-Oxides

Miyaji, R.; Asano, K.; Matsubara, S.

J. Am. Chem. Soc. 2015, 137, 6766–6769.

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Facile Net Cycloaddition Approach to Optically Active 1,5‑Benzothiazepines
Fukata, Y.; Asano, K.; Matsubara, S.
J. Am. Chem. Soc. 2015, 137, 5320–5323.
Highlighted in Synfacts 2015, 11, 770.
Highlighted in J. Synth. Org. Chem., Jpn. 2015, 73, 1162.

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Nickel-catalyzed Dual C–C σ Bond Activation to Construct Carbocyclic Skeletons

Nakai, K.; Kurahashi, T.; Matsubara, S.

Tetrahedron 2015, 71, 4512–4517.

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Nickel-catalysed Synthesis of Tetrasubstituted Vinyl Sulfides from Thiocarbamates and Internal Alkynes

Inami, T.; Kurahashi, T.; Matsubara, S.

Chem. Commun. 2015, 51, 1285–1288.

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Reasons Two Nonstrained C–C σ-Bonds Can Be Easily Cleaved in Decyanative [4 + 2] Cycloaddition Catalyzed by Nickel(0)/Lewis Acid Systems. Theoretical Insight

Guan, W.; Sakaki, S.; Kurahashi, T.; Matsubara, S.

ACS Catal. 2015, 5, 1–10.

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Preparation of Cycloheptane Ring by Nucleophilic Cyclopropanation of 1,2-Diketones with

Bis(iodozincio)methane

Haraguchi, R.; Takada, Y.; Matsubara, S.

Org. Biomol. Chem. 2015, 13, 241–247.

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