熊谷 直哉 (クマガイ ナオヤ)

Kumagai, Naoya

写真a

所属(所属キャンパス)

薬学部 薬科学科 (芝共立)

職名

教授

HP

外部リンク

経歴 【 表示 / 非表示

  • 2005年04月
    -
    2006年03月

    ハーバード大学, 生物化学科, ポストドクトラルフェロー

  • 2006年04月
    -
    2010年03月

    東京大学, 大学院薬学系研究科, 助教

  • 2010年04月
    -
    2010年12月

    微生物化学研究所, 有機合成研究部, 研究員

  • 2010年04月
    -
    2017年03月

    立教大学, 理学部, 兼任講師

  • 2011年01月
    -
    2013年03月

    微生物化学研究所, 有機合成研究部, 主任研究員

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学歴 【 表示 / 非表示

  • 1996年04月
    -
    2000年03月

    東京大学, 薬学部

    大学, 卒業

  • 2000年04月
    -
    2002年03月

    東京大学, 大学院薬学系研究科

    大学院, 修了, 修士

  • 2002年04月
    -
    2005年03月

    東京大学, 大学院薬学系研究科

    大学院, 修了, 博士

学位 【 表示 / 非表示

  • 東京大学, 東京大学, 課程, 2005年03月

免許・資格 【 表示 / 非表示

  • 薬剤師, 2000年09月

  • 第一種放射線管理主任者, 2012年04月

 

著書 【 表示 / 非表示

  • Interplay of diamides and rare earth metals: Specific molecular spaces and catalytic activity

    Kumagai N., Shibasaki M., Designed Molecular Space in Material Science and Catalysis, 2018年01月

     概要を見る

    A catalytic system comprising functionalized small diamides and rare earth metals (REs) exerts intriguing catalytic properties that are dictated by dynamic construction of flexible molecular spaces. The dynamic interaction of diamides and REs is characterized by broad applicability to distinct reaction systems as well as notable switchable catalysis. Structural modification of the diamide allows for enhanced intermolecular interactions to afford a self-assembled solid-phase catalyst with a specific molecular space that engages in heterogeneous asymmetric catalysis with a continuous-flow platform.

  • Chiral Bimetallic Lewis Acids

    Shibasaki M., Kumagai N., Topics in Organometallic Chemistry, 2018年

     概要を見る

    Here, we review the utility of chiral bimetallic (multimetallic) Lewis acidic complexes in catalytic asymmetric transformations. Bimetallic complexes are endowed with dual catalytic functions that synergistically activate multiple substrates and functionalities. This cooperative activation mode is particularly effective for activating low reactivity substrates in a highly stereoselective manner without the aid of stoichiometric activating reagents. The privileged bimetallic catalysts presented here highlight the importance of catalyst design in the development of widely applicable catalytic systems.

論文 【 表示 / 非表示

  • Strategic Synthesis of Asymmetrically Substituted C4N4 Fluorophores

    Xu W., Kohei M., Shibasaki M., Kumagai N.

    Synthesis (Germany) (Synthesis (Germany))  53 ( 18 ) 3355 - 3360 2021年09月

    ISSN  00397881

     概要を見る

    C4N4 fluorophores comprise a recently disclosed new class of emissive organic molecules with modular synthetic capabilities. Herein, we report a new synthetic protocol toward asymmetrically di arylated C4N4 fluorescent materials. Direct monoarylation of 1-naphthol is exploited to suppress undesired diarylation and to provide a free phenolic hydroxy group for prospective linking to a molecule of interest. Installation of the second aromatic unit in order to acquire fluorescent properties is achieved by Suzuki-Miyaura cross-coupling.

  • Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes

    Saito A., Adachi S., Kumagai N., Shibasaki M.

    Angewandte Chemie - International Edition (Angewandte Chemie - International Edition)  60 ( 16 ) 8739 - 8743 2021年04月

    ISSN  14337851

     概要を見る

    A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.

  • Highly Enantio- And Diastereoselective Synthesis of 1,2,3-Trisubstituted Cyclopropanes from α,β-Unsaturated Amides and Stabilized Sulfur Ylides Catalyzed by a Chiral Copper(I) Complex

    Pagire S.K., Kumagai N., Shibasaki M.

    ACS Catalysis (ACS Catalysis)     11597 - 11606 2021年

     概要を見る

    The stereoselective preparation of 1,2,3-substituted cyclopropanes from α,β-unsaturated carbonyl compounds in the carboxylic acid oxidation state through Michael addition-initiated ring-closure reactions is a significant challenge in organic synthesis. Herein, the previously elusive catalytic asymmetric cyclopropanation of α,β-unsaturated amides with stabilized sulfur ylides has been efficiently accomplished utilizing a chiral Cu(I) complex. This Lewis acid catalytic system effectively converts a wide range of electron-deficient alkenes into the corresponding 1,2,3-trisubstituted cyclopropanes under mild reaction conditions in good to excellent yields with both high to excellent enantio- and diastereoselectivities. The resulting enantiomerically enriched cyclopropane amides can be readily diversified into promising synthetic intermediates such as β-aminocyclopropanecarboxylic acids with the facile recovery of the 7-azaindoline auxiliary without influencing the optical purity of the cyclopropane unit, which highlights the synthetic efficacy of this catalytic approach.

  • Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Aldehydes

    Balaji P.V., Li Z., Saito A., Kumagai N., Shibasaki M.

    Chemistry - A European Journal (Chemistry - A European Journal)  26 ( 67 ) 15524 - 15527 2020年12月

    ISSN  09476539

     概要を見る

    A fluorine-containing tetrasubstituted stereogenic center is a highly valued structural feature in medicinal chemistry. Herein, we describe the direct coupling of racemic α-fluoronitriles and aldehydes promoted by a chiral CuI/Barton's base catalytic system, delivering α-tetrasubstituted α-fluoro-β-hydroxynitriles with satisfactory stereoselection. The stereochemical course was positively biased by the combined use of asymmetrical achiral thiourea as a supplementary ligand for CuI, which significantly enhanced the stereoselectivity. Both aromatic and aliphatic aldehydes were implemented to provide densely and stereoselectively functionalized chiral building blocks with aliphatic and aromatic tails.

  • The Different Faces of [Ru(bpy)<inf>3</inf>Cl<inf>2</inf>] and fac[Ir(ppy)<inf>3</inf>] Photocatalysts: Redox Potential Controlled Synthesis of Sulfonylated Fluorenes and Pyrroloindoles from Unactivated Olefins and Sulfonyl Chlorides

    Pagire S.K., Kumagai N., Shibasaki M.

    Organic Letters (Organic Letters)  22 ( 20 ) 7853 - 7858 2020年10月

    ISSN  15237060

     概要を見る

    A cascade alkene sulfonylation that simultaneously forges C-S and C-C bonds is a highly efficient and powerful approach for directly accessing structurally diverse sulfonylated compounds in a single operation. The reaction was enabled by visible-light-mediated regioselective radical addition of sulfonyl chlorides to 2-arylstyrenes using fac[Ir(ppy)3] as a photocatalyst, demonstrating its unique role in a photocascade process to execute atom transfer radical addition (ATRA) followed by photocyclization. A new class of sulfonyl-substituted fluorenes and pyrroloindoles, which are useful in the field of photoelectronic materials and medicinal chemistry, was produced in excellent yields by this photocascade reaction. In contrast, the cyclization was interrupted when using the [Ru(bpy)3Cl2] catalyst having lower reduction potential, leading only to the formation of a C-S bond and the production of acyclic sulfonylated 2-arylstyrenes under identical reaction conditions. The synthetic utility of the present room-temperature photocatalysis is enhanced by the broad availability of bench-stable sulfonyl chlorides and unactivated olefins, thereby providing a cost-effective and broad-scope protocol.

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競争的資金等の研究課題 【 表示 / 非表示

  • 戦略的分子デザインが拓く分子変換化学

    2020年04月
    -
    2023年03月

    文部科学省・日本学術振興会, 科学研究費助成事業, 熊谷 直哉, 基盤研究(B), 補助金,  代表

 

担当授業科目 【 表示 / 非表示

  • 課題研究(分子創成化学)

    2021年度

  • 演習(分子創成化学)

    2021年度

  • 卒業研究1(薬学科)

    2021年度

  • 英語演習(薬学科)

    2021年度

  • 医薬分子設計化学

    2021年度

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