Development of Catalytic Asymmetric C–C Bond-Forming Reactions Using Alkylnitriles as Pronucleophiles

• Project Area: Precise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions
• Project/Area Number: 16H01043
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Microbial Chemistry Research Foundation
• Principal Investigator: 熊谷 直哉 公益財団法人微生物化学研究会, 微生物化学研究所, 主席研究員 (40431887)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000); Fiscal Year 2017: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000); Fiscal Year 2016: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
• Keywords: ニトリル / 不斉触媒 / 原子効率 / 光学活性 / C-C結合 / 不斉反応 / 触媒反応 / 環境調和型反応

Outline of Annual Research Achievements

益々高まるフッ素含有キラルビルディングブロック群の需要を鑑み，α-フルオロニトリルを基質とするイミンへのダイレクト型触媒的不斉付加反応の開発に注力した。3置換炭素のC-H結合をC-Fに変換した誘導体群の導出を狙い，フッ素含有4置換不斉中心を与えるα-フルオロベンジルニトリルを用いて初期検討を行った。N-ジフェニルホスフィノイルイミンが高い反応性を示し，ソフトなLewis酸触媒としてCu(I)錯体がα-フルオロニトリルを官能基選択的に活性化し，共存するBarton塩基により系内発生したシアノカルバニオンの円滑な付加反応が確認された。(R)-DTBM-Segphosが優れたエナンチオ選択性を発現させることを見出したが，リガンドスクリーニングによるジアステレオ選択性の発現は困難を極めた。副次的な立体制御をアシストするソフトLewis塩基性添加剤を探索した結果，触媒量の非対称チオウレアによりジアステレオ選択性が大幅に向上することを突き止めた。チオウレアのN上の置換基パターンと立体選択性および化学収率には強い相関関係が認められ，イミンへの付加段階に直接的に関与していることが強く示唆されている。NMRおよびMS解析によりチオウレアのCu(I)への競合的配位が観測されており，現在速度論解析も含めてその効果を精査している。今後，イミンおよびα-フルオロニトリルの一般性を確認し，光学活性生成物ニトリル基の変換多様性も提示して，新しいキラルビルディングブロック合成法として報告する予定である。

Research Progress Status

29年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

29年度が最終年度であるため、記入しない。

Research Products

• [Journal Article] Bis(2-pyridyl)amides as Readily Cleavable Amides Under Cataly1c, Neutral, and Room-Temperature Conditions (2018)
  • Author(s): Shinya Adachi, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Synlett Volume: 29 Issue: 03 Pages: 301-305
  • DOI: 10.1055/s-0036-1590932
  • Peer Reviewed
• [Journal Article] Structural and Computational Investigation of Intramolecular N...H Interactions in α- and β-Fluorinated 7-Azaindoline Amides (2018)
  • Author(s): Lennart Brewitz, Hidetoshi Noda, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Eur. J. Org. Chem. Volume: - Issue: 6 Pages: 714-722
  • DOI: 10.1002/ejoc.201701083
  • Peer Reviewed
• [Journal Article] Synthetic Studies of Viridiofungins, Broad-Spectrum Antifungal Agents and Serine Palmitoyl Transferase Inhibitors (2018)
  • Author(s): Naoya Kumagai, Masakatsu Shibasaki
  • Journal Title: The Journal of Antibiotics, Volume: 71 Issue: 1 Pages: 53-59
  • DOI: 10.1038/ja.2017.110
  • Peer Reviewed
• [Journal Article] Heterogeneous Heterobimetallic Catalysis Enabling Expeditious Access to CF3-Containing vic-Amino Alcohols (2018)
  • Author(s): Tomoya Karasawa, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Org. Lett. Volume: 20 Issue: 1 Pages: 308-311
  • DOI: 10.1021/acs.orglett.7b03767
  • Peer Reviewed
• [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage (2018)
  • Author(s): Jin Cui, Akimichi Ohtsuki, Takumi Watanabe, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Chem. Eur. J. Volume: 24 Issue: 11 Pages: 2598-2601
  • DOI: 10.1002/chem.201800020
  • Peer Reviewed
• [Journal Article] Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives (2018)
  • Author(s): Bo Sun, Roman Pluta, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Org. Lett. Volume: 20 Issue: 3 Pages: 526-529
  • DOI: 10.1021/acs.orglett.7b03609
  • Peer Reviewed
• [Journal Article] Conquering amide planarity: Structural distortion and its hidden reactivity (2018)
  • Author(s): Shinya Adachi, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Tetrahedron Lett. Volume: 59 Issue: 13 Pages: 1147-1158
  • DOI: 10.1016/j.tetlet.2018.01.097
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Synthesis of α-Trifluoromethylated Carbinols: A Case Study of Tertiary Propargylic Alcohols (2018)
  • Author(s): Hidetoshi Noda, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Asian J. Org. Chem. Volume: 7 Issue: 4 Pages: 599-612
  • DOI: 10.1002/ajoc.201800013
  • Peer Reviewed / Open Access
• [Journal Article] Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands (2018)
  • Author(s): Zhao Li, Hidetoshi Noda, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Tetrahedron Volume: in press Issue: 26 Pages: 3301-3305
  • DOI: 10.1016/j.tet.2018.03.073
  • Peer Reviewed
• [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide (2018)
  • Author(s): Toshifumi Takeuchi, Naoya Kumagai, Masakatsu Shibasaki
  • Journal Title: Journal of Organic Chemistry Volume: 83 Issue: 10 Pages: 5851-5858
  • DOI: 10.1021/acs.joc.8b00743
  • Peer Reviewed
• [Journal Article] Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides (2018)
  • Author(s): Zhongdong Sun, Bo Sun, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Org. Lett., Volume: in press Issue: 10 Pages: 3070-3073
  • DOI: 10.1021/acs.orglett.8b01109
  • Peer Reviewed
• [Journal Article] Cu/Pd Synergistic Dual Catalysis: Asymmetric a-Allylation of an a-CF3 Amide (2017)
  • Author(s): Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
  • Journal Title: Angewandte Chemie International Edition Volume: 56 Issue: 20 Pages: 5551-5555
  • DOI: 10.1002/anie.201702113
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] α-Halo Amides as Competent Latent Enolates: DirectCatalytic Asymmetric Mannich-type Reaction (2017)
  • Author(s): Bo Sun, Pandur Venkatesan Balaji, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: J. Am. Chem. Soc. Volume: 139 Issue: 24 Pages: 8295-8301
  • DOI: 10.1021/jacs.7b03291
  • Peer Reviewed
• [Journal Article] α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric Exo-selective 1,3-Dipolar Cycloaddition with Nitrones (2017)
  • Author(s): Ming Zhang, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Chem. Eur. J. Volume: 23 Issue: 51 Pages: 12450-12455
  • DOI: 10.1002/chem.201702330
  • Peer Reviewed
• [Journal Article] Direct N-acylation of sulfoximines with carboxylic acids catalyzed by the B3NO2 heterocycle (2017)
  • Author(s): Hidetoshi Noda, Yasuko Asada, Masakatsu Shibasaki* Naoya Kumagai*
  • Journal Title: Chem. Commun. Volume: 53 Issue: 54 Pages: 7447-7450
  • DOI: 10.1039/c7cc03386a
  • Peer Reviewed
• [Journal Article] Photocatalytic α-acylation of ethers (2017)
  • Author(s): Zhongdong Sun, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Org. Lett. Volume: 19 Issue: 14 Pages: 3727-3730
  • DOI: 10.1021/acs.orglett.7b01552
  • Peer Reviewed
• [Journal Article] Direct catalytic asymmetric aldol addition an α-CF3 amide to arylglyoxal hydrates (2017)
  • Author(s): Akinobu Matsuzawa, Hidetoshi Noda, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: J. Org. Chem. Volume: 82 Issue: 15 Pages: 8304-8308
  • DOI: 10.1021/acs.joc.7b01381
  • Peer Reviewed
• [Journal Article] Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: preparation of (R)-diethyl(1-amino-1-phenylethyl)phosphonate (2017)
  • Author(s): Shaoquan Lin, Yasunari Otsuka, Liang Yin, Naoya Kumagai*, Masakatsu Shibasaki*
  • Journal Title: Org. Synth. Volume: 94 Pages: 313-331
  • DOI: 10.15227/orgsyn.094.0313
  • Peer Reviewed
• [Journal Article] Strategic Immobilization of Molecular Catalysts onto Carbon Nanotubes via Noncovalent Interaction for Catalytic Organic Transformations (2017)
  • Author(s): Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Isr, J. Chem. Volume: 57 Issue: 3-4 Pages: 270-278
  • DOI: 10.1002/ijch.201600126
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Pyramidalization/Twisting of the Amide Functional Group via Remote Steric Congestion Triggered by Metal Coordination (2017)
  • Author(s): Shinya Adachi, Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Chem. Sci. Volume: 8 Issue: 1 Pages: 85-90
  • DOI: 10.1039/c6sc03669d
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Catalytic Asymmetric Synthesis of 2,3,3,3-Ttrafluoro-2-Methyl-1-Arylpropan-1-Amines as Useful Building Blocks for SAR-Studies (2017)
  • Author(s): Lennart Brewitz, Naoya Kumagai,* and Masakatsu Shibasaki*
  • Journal Title: J. Fluor. Chem. Volume: 194 Pages: 1-7
  • DOI: 10.1016/j.jfluchem.2016.12.008
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides (2017)
  • Author(s): Zijian Liu, Toshifumi Takeuchi, Roman Pluta, Fernando Arteaga Arteaga, Naoya Kumagai,* and Masakatsu Shibasaki*
  • Journal Title: Org. Lett. Volume: 19 Issue: 3 Pages: 710-713
  • DOI: 10.1021/acs.orglett.6b03890
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Asymmetric flow catalysis: Mix-and-go solid-phase Nd/Na catalyst for expeditious enantioselective access to a key intermediate of AZD7594 (2017)
  • Author(s): Akihito Nonoyama, Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Tetrahedron Volume: 73 Issue: 11 Pages: 1517-1521
  • DOI: 10.1016/j.tet.2017.01.066
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding (2017)
  • Author(s): Christopher R. Opie, Naoya Kumagai,* and Masakatsu Shibasaki*
  • Journal Title: Angew. Chem., Int. Ed. Volume: 56 Issue: 12 Pages: 3349-3353
  • DOI: 10.1002/anie.201610279
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Unique Physicochemical Catalytic Properties Dictated by the B3NO2 Ring System (2017)
  • Author(s): Hidetoshi Noda, Makoto Furutachi, Yasuko Asada, Masakatsu Shibasaki,* and Naoya Kumagai*
  • Journal Title: Nat. Chem. Volume: in press Issue: 6 Pages: 571-577
  • DOI: 10.1038/nchem.2708
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide (2017)
  • Author(s): Hidetoshi Noda, Fuyuki Amemiya, Karin Weidner, Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Chem. Sci. Volume: 8 Issue: 4 Pages: 3260-3269
  • DOI: 10.1039/c7sc00330g
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides (2016)
  • Author(s): Fernando Arteaga Arteaga, Zijian Liu, Lennart Brewitz, Jianyang Chen, Bo Sun, Naoya Kumagai, and Masakatsu Shibasaki
  • Journal Title: Org. Lett. Volume: 18 Issue: 10 Pages: 2391-2394
  • DOI: 10.1021/acs.orglett.6b00879
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Nucleophilic and Electrophilic Activation of Non-Heteroaromatic Amides in Atom Economical Asymmetric Catalysis (2016)
  • Author(s): Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Chem. Eur. J. Volume: 22 Issue: 43 Pages: 15192-15200
  • DOI: 10.1002/chem.201602484
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Enantioselective Synthesis of α,α-Disubstituted α-Amino Acids via Direct Catalytic Asymmetric Addition of Acetonitrile to α-Iminoesters (2016)
  • Author(s): Shaoquan Lin, Naoya Kumagai,* Masakatsu Shibasaki*
  • Journal Title: Org. Biomol. Chem. Volume: 14 Issue: 41 Pages: 9725-9730
  • DOI: 10.1039/c6ob01874b
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] Reaction Development in the Amide Playground (2018)
  • Author(s): Naoya Kumagai
  • Organizer: Princeton University
  • Int'l Joint Research / Invited
• [Presentation] Reaction Development in the Amide Playground (2018)
  • Author(s): Naoya Kumagai
  • Organizer: University of Michigan
  • Int'l Joint Research / Invited
• [Presentation] Reaction Development in the Amide Playground (2018)
  • Author(s): Naoya Kumagai
  • Organizer: California Institute of Technology
  • Int'l Joint Research / Invited
• [Presentation] Reaction Development in the Amide Playground (2018)
  • Author(s): Naoya Kumagai
  • Organizer: University of Utah
  • Int'l Joint Research / Invited
• [Presentation] トリフルオロメチルケトンの直接的触媒的不斉ニトロアルドール反応 (2018)
  • Author(s): 柄澤智哉、熊谷直哉、柴﨑正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] 周辺立体環境因子によるアミドの活性化 (2018)
  • Author(s): 足立慎弥、熊谷直哉、柴﨑正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] Asymmetric Catalytic 1,6-Conjugate Addition of para-Quinone Methides Using 7-Azaindoline Amides (2018)
  • Author(s): 孫仲冬、熊谷直哉、柴﨑正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] ピリミジン型DATB：簡便合成が可能なアミド化触媒 (2018)
  • Author(s): Christopher Opie、野田秀俊、柴﨑正勝、熊谷直哉
  • Organizer: 日本薬学会第138年会
• [Presentation] Catalytic Oligopeptide Synthesis (2018)
  • Author(s): 劉子建、野田秀俊、柴﨑正勝、熊谷直哉
  • Organizer: 日本薬学会第138年会
• [Presentation] ダイレクト型触媒的不斉マンニッヒ型反応によるα-ヒドロキシ-β-アミノ酸誘導体の不斉合成 (2018)
  • Author(s): Roman Pluta、Bo Sun、熊谷直哉、柴崎正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage (2018)
  • Author(s): 崔進、大朏彰道、渡辺匠、熊谷直哉、柴﨑正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] Direct Catalytic Asymmetric Addition of α-Aryl α-Fluoro Acetonitrile to Imines (2018)
  • Author(s): Pandur Balaji、Lennart Brewitz、熊谷直哉, 柴崎正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] B3NO2 へテロ環を触媒とする直接的アミド化反応の反応機構解析 (2018)
  • Author(s): 野田秀俊、朝田康子、柴﨑正勝、熊谷直哉
  • Organizer: 日本薬学会第138年会
• [Presentation] 不斉配位子―遷移金属触媒によるアルキルニトリル類のアルデヒド類への不斉付加反応の開発 (2018)
  • Author(s): 大朏彰道、Youmei Bao、Shaoquan Lin、熊谷直哉、柴﨑正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] シアノ基の求電子的多重活性化を指向した2 核金属錯体の合成研究 (2018)
  • Author(s): 齊藤誠、熊谷直哉、柴崎正勝
  • Organizer: 日本薬学会第138年会
• [Presentation] In(OTf)3-BHA 触媒を用いたニトロンのα , β - 不飽和7- アザインドリンアミドへのエキソ選択的不斉1,3-双極子付加環化反応 (2017)
  • Author(s): 張 明, 熊谷 直哉, 柴﨑 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C201 (宮城県, 仙台市）
  • Year and Date: 2017-03-27
• [Presentation] 光異性化と特異的水素結合による立体選択的可逆フォールディング (2017)
  • Author(s): Chris Opie, 熊谷 直哉, 柴崎 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C201 (宮城県, 仙台市）
  • Year and Date: 2017-03-27
• [Presentation] α - アジド-7- アザインドリンアミドを用いたアルキニルトリフルオロメチルケトンへのダイレクト型触媒的不斉アルドール反応の開発 (2017)
  • Author(s): 雨宮 冬樹, 野田 秀俊, Weidner Karin, 熊谷 直哉, 柴崎 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C201 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] α -Cl 及びBr アミドのダイレクト型触媒的不斉Mannich 反応 (2017)
  • Author(s): 孫 博, Pandur Venkatesan Balaji, 熊谷 直哉,柴崎 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C202 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] 新規複核ホウ素ヘテロ環を触媒とする直接的アミド化反応の開発 (2017)
  • Author(s): 野田 秀俊, 古舘 信, 朝田 康子, 柴崎 正勝, 熊谷直哉
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C202 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] 光触媒・Ni 触媒によるエーテルのα -C(sp3)-H 官能基化反応 (2017)
  • Author(s): 孫 仲冬, 熊谷 直哉, 柴﨑 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C202 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] Cu/Pd バイナリー型触媒を用いたα -CF3 アミドのα - 不斉アリル化反応 (2017)
  • Author(s): 齊藤 誠, 熊谷 直哉, 柴﨑 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C205 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] 金属配位誘起による立体因子に起因する非平面アミドの探索 (2017)
  • Author(s): 足立 慎弥, 熊谷 直哉, 柴崎 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C205 (宮城県, 仙台市）
  • Year and Date: 2017-03-26
• [Presentation] アルキルアミドのダイレクト型触媒的不斉アルドール反応 (2017)
  • Author(s): Zijian Liu, Toshifumi Takeushi, Roman Krzysztof Pluta, Fernando Arteaga Arteaga, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C202 (宮城県, 仙台市）
  • Year and Date: 2017-03-25
• [Presentation] カーボンナノチューブに固定化したNd/Na異種2核金属触媒による高効率的なフロー系ニトロアルドール反応の開発 (2017)
  • Author(s): 野々山 彰人, 熊谷 直哉, 柴崎 正勝
  • Organizer: 日本薬学会第137年会
  • Place of Presentation: 東北大学川内北キャンパスC棟 2F C202 (宮城県, 仙台市）
  • Year and Date: 2017-03-25
• [Presentation] アミドをplaygroundとした触媒反応設計 (2017)
  • Author(s): 熊谷 直哉
  • Organizer: 化成品工業協会
  • Place of Presentation: 大阪化学技術センター (大阪府, 大阪市）
  • Year and Date: 2017-03-08
  • Invited
• [Presentation] アミドをplaygroundとした触媒反応設計 (2017)
  • Author(s): 熊谷 直哉
  • Organizer: 化成品工業協会
  • Place of Presentation: 東京都, 港区赤坂
  • Year and Date: 2017-02-22
  • Invited
• [Presentation] アルキルニトリルを求核種前駆体とする触媒的不斉C-C結合形成反応 (2017)
  • Author(s): 熊谷 直哉
  • Organizer: 新学術領域研究「精密制御反応場」第２回公開シンポジウムプログラム
  • Place of Presentation: 名古屋大学ES総合館１階ESホール (愛知県, 名古屋市）
  • Year and Date: 2017-01-26
• [Presentation] Development of catalytic asymmetric C-C bond-forming reactions using alkylnitriles as pronucleophiles (2017)
  • Author(s): Shaoqan Lin, Youmei Bao, Akimichi Ohtsuki, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: 2nd International Symposium on Precisely Designed Catalysts with Customized Scaffolding
  • Int'l Joint Research
• [Presentation] α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-type Reaction (2017)
  • Author(s): Bo Sun，Pandur Venkatesan Balaji, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: 第15回次世代を担う有機化学シンポジウム
• [Presentation] Reaction Development in the Amide Playground (2017)
  • Author(s): Naoya Kumagai
  • Organizer: Shanghai Institute of Organic Chemistry (SIOC)
  • Int'l Joint Research / Invited
• [Presentation] DATB Catalysis: Efficient Catalytic Direct Amidation Promoted by the B3NO2 Heterocycle (2017)
  • Author(s): Naoya Kumagai
  • Organizer: International Symposium on Pure and Applied Chemistry 2017 (ISPAC)
  • Int'l Joint Research / Invited
• [Presentation] Reaction Development in the Amide Playground (2017)
  • Author(s): Naoya Kumagai
  • Organizer: University of Ludwig-Maximilians University Munchen
  • Int'l Joint Research / Invited
• [Presentation] Reaction Development in the Amide Playground (2017)
  • Author(s): Naoya Kumagai
  • Organizer: University of Munster
  • Int'l Joint Research / Invited
• [Presentation] Asummetric α-Allylation of α-CF3 Amide Promoted by Cu/Pd Synergistic Catalyst (2017)
  • Author(s): Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: The19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis(OMCOS 19)
  • Int'l Joint Research
• [Presentation] Direct Catalytic Aldol Reaction of α-N3 Amide for the Asymmetric Synthesis of CF3-Substituted tertiary Propargylic Alcohols (2017)
  • Author(s): Hidetoshi Noda, Fuyuki Amemiya, Karin Weidner, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: The19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis(OMCOS 19)
  • Int'l Joint Research
• [Presentation] Reaction Development in the Amide Playground (2017)
  • Author(s): Naoya Kumagai
  • Organizer: Stockholm University
  • Int'l Joint Research / Invited
• [Presentation] Reversible stereoselective folding/Unfolding fueled by the interplay of photoisomerism and hydrogen bonding (2017)
  • Author(s): Christopher Opie, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: RACI National Centenary Conference 2017
  • Int'l Joint Research
• [Presentation] 周辺立体環境因子によるアミドの活性化 (2017)
  • Author(s): 足立慎弥、熊谷直哉、柴崎正勝
  • Organizer: 第28回基礎有機化学討論会
• [Presentation] Topics in Amide Chemistry (2017)
  • Author(s): Naoya Kumagai
  • Organizer: OIST: Okinawa Institute of Science & Technology
  • Invited
• [Presentation] α-アジド-7-アザインドリンアミドを用いたアルキニルトリフルオロメチルケトンへのダイレクト型触媒的不斉アルドール反応の開発 (2017)
  • Author(s): 雨宮冬樹、野田秀俊、Karin Weidner、熊谷直哉、柴崎正勝
  • Organizer: 第61回日本薬学会関東支部大会
• [Presentation] 完璧な反応デザインで完璧な未来分子を作る (2017)
  • Author(s): 熊谷 直哉
  • Organizer: 第59回天然有機化合物討論会
  • Invited
• [Presentation] 複核ホウ素ヘテロ環DATBの化学：直接的アミド化触媒への展開 (2017)
  • Author(s): 野田秀俊、古館信、Zijian Liu、朝田康子、柴崎正勝、熊谷直哉
  • Organizer: 第43回反応と合成の進歩シンポジウム
• [Presentation] Catalytic Oligopeptide Synthesis (2017)
  • Author(s): Zijian Liu、野田秀俊、柴﨑正勝、熊谷直哉
  • Organizer: 第54回ペプチド討論会
• [Presentation] アミドをPlayGroundとした反応設計 (2017)
  • Author(s): 熊谷 直哉
  • Organizer: 京都大学 第2回有機若手ワークショップ
  • Invited
• [Presentation] アミドをplaygroundにした反応設計 (2016)
  • Author(s): 熊谷 直哉
  • Organizer: 名古屋大学 ITbM/IGER Chemistry Workshop 2016
  • Place of Presentation: 名古屋大学ESホール (愛知県, 名古屋市）
  • Year and Date: 2016-12-19
  • Invited
• [Presentation] 新規複核ホウ素ヘテロ環の設計,合成,及びアミド化触媒への展開 (2016)
  • Author(s): 野田 秀俊・古舘 信・朝田 康子・柴崎 正勝・熊谷 直哉
  • Organizer: 第43回有機典型元素化学討論会
  • Place of Presentation: 仙台市民会館 (宮城県, 仙台市）
  • Year and Date: 2016-12-10
• [Presentation] アミドのダイレクト型アルドール反応を基軸とした含フッ素3級プロパルギルアルコールの触媒的不斉合成 (2016)
  • Author(s): 野田秀俊、雨宮冬樹、Karin Weidner、熊谷直哉、柴崎正勝
  • Organizer: 第42回反応と合成の進歩シンポジウム
  • Place of Presentation: 静岡市清水文化会館マリナート (静岡県, 静岡市）
  • Year and Date: 2016-11-08
• [Presentation] 分子配列・分子空間を意識した反応設計 (2016)
  • Author(s): 熊谷直哉
  • Organizer: 新領域研究グループ「精密物質変換のための分子空間化学」 2016シンポジウム
  • Place of Presentation: 長崎大学 (長崎県, 長崎市）
  • Year and Date: 2016-09-05
• [Presentation] 金属配位誘起による立体因子に起因する非平面アミドの探索 (2016)
  • Author(s): 足立慎弥、熊谷直哉、柴崎正勝
  • Organizer: 第27回基礎有機化学討論会
  • Place of Presentation: 広島国際会議場 (広島県, 広島市）
  • Year and Date: 2016-09-02
• [Presentation] Direct Catalytic Asymmetric C-C Bond-Forming Reactions via Catalytic Enolization of Amide (2016)
  • Author(s): Toshifumi Takeuchi, Karin Weidner, Liang Yin, Lennart Brewitz, Zhongdong Sun, Fernando A. Arteaga, Zijian Liu, Chen Jianyang, Bo Sun, Naoya Kumagai, and Masakatsu Shibasaki
  • Organizer: International Symposium on Homogeneous Catalysis ISHC 20
  • Place of Presentation: 京都テレサ (京都府, 京都市）
  • Year and Date: 2016-07-14
  • Int'l Joint Research
• [Presentation] A Multiboton Catalyst for General Direct Amidation (2016)
  • Author(s): Hidetoshi Noda, Makoto Furutachi, Yasuko Asada, Masakatsu Shibasaki, Naoya Kumagai
  • Organizer: The 15th Belgian Organic Synthesis Symposium Antwerp
  • Place of Presentation: University of Antwerp (Belgium)
  • Year and Date: 2016-07-11
  • Int'l Joint Research
• [Presentation] Exploration of Cooperative Asymmetric Catalysts Toward Efficient Synthesis of Therapeutics (2016)
  • Author(s): Naoya Kumagai
  • Organizer: University of Oxford 講演会
  • Place of Presentation: University of Oxford (UK)
  • Year and Date: 2016-07-07
  • Int'l Joint Research / Invited
• [Presentation] Exploration of Cooperative Asymmetric Catalysts Toward Efficient Synthesis of Therapeutics (2016)
  • Author(s): Naoya Kumagai
  • Organizer: University of Cambridge 講演会
  • Place of Presentation: University of Cambridge (UK)
  • Year and Date: 2016-07-06
  • Int'l Joint Research / Invited
• [Presentation] Exploration of Cooperative Asymmetric Catalysts Toward Efficient Synthesis of Therapeutics (2016)
  • Author(s): Naoya Kumagai
  • Organizer: University of Bristol 講演会
  • Place of Presentation: University of Bristol (UK)
  • Year and Date: 2016-07-04
  • Int'l Joint Research / Invited
• [Presentation] Cu/Pdバイメタリック触媒によるα-CF3アミドのα-不斉アリル化反応 (2016)
  • Author(s): 齊藤誠、熊谷直哉、柴崎正勝
  • Organizer: 第109回有機合成シンポジウム
  • Place of Presentation: 東京工業大学（大岡山キャンパス）ディジタル多目的ホール、コラボレーションルーム (東京都, 目黒区）
  • Year and Date: 2016-06-08
• [Presentation] 新規複核ホウ素触媒を用いた直接的アミド化反応の開発 (2016)
  • Author(s): 野田秀俊，古舘 信，朝田康子，柴崎正勝，熊谷直哉
  • Organizer: 第14回次世代を担う有機化学シンポジウム
  • Place of Presentation: 長井記念ホール (東京都, 渋谷区）
  • Year and Date: 2016-05-27
• [Presentation] α-アジド-7-アザインドリンアミドを用いたトリフルオロメチルケトンへのダイレクト型触媒的不斉アルドール反応の開発 (2016)
  • Author(s): 雨宮冬樹、野田秀俊、Karin Weidner、熊谷直哉、柴崎正勝
  • Organizer: 第 71 回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京農工大学小金井キャンパス講義棟 （東京都, 小金井市）
  • Year and Date: 2016-05-14
• [Presentation] 安価・安定なNd塩を用いるNd/Na異種2核金属触媒の新規調製法の開発 (2016)
  • Author(s): 野々山彰人、橋本和樹、齊藤誠、熊谷直哉、柴﨑正勝
  • Organizer: 第 71 回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京農工大学小金井キャンパス講義棟 （東京都, 小金井市）
  • Year and Date: 2016-05-14
• [Presentation] Electrophilic Activation of α,β-Unsaturated Amide: Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated γ-Butyrolactone (2016)
  • Author(s): Ming Zhang, Naoya Kumagai, Masakatsu Shibasaki
  • Organizer: Molecular Chirality Asia 2016
  • Place of Presentation: Knowledge Capital Congres Convention Center (大阪府, 大阪市）
  • Year and Date: 2016-04-20
  • Int'l Joint Research
• [Remarks] 公益財団法人微生物化学研究会 微生物化学研究所 有機合成研究部
  • URL: http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index.html
• [Remarks] 微生物化学研究所・有機合成研究部
  • URL: http://www.bikaken.or.jp/laboratories/organic/summary.html
• [Patent(Industrial Property Rights)] 化合物、及び発光化合物 (2017)
  • Inventor(s): 野田秀俊、朝田康子、柴﨑正勝、熊谷直哉
  • Industrial Property Rights Holder: 公益財団法人微生物化学研究会
  • Industrial Property Rights Type: 特許
  • Filing Date: 2017
• [Patent(Industrial Property Rights)] 触媒、アミド結合の形成方法、及びアミド化合物の製造方法 (2017)
  • Inventor(s): Christopher Opie、野田秀俊、柴﨑正勝、熊谷直哉
  • Industrial Property Rights Holder: 公益財団法人微生物化学研究会
  • Industrial Property Rights Type: 特許
  • Filing Date: 2017
• [Patent(Industrial Property Rights)] 触媒、アミド結合の形成方法、及びアミド化合物の製造方法 (2016)
  • Inventor(s): 熊谷直哉、野田秀俊、古舘 信、朝田康子、柴﨑正勝
  • Industrial Property Rights Holder: 公益財団法人微生物化学研究会
  • Industrial Property Rights Type: 特許
  • Filing Date: 2016-11-21
  • Overseas
• [Patent(Industrial Property Rights)] 触媒、アミド結合の形成方法、及びアミド化合物の製造方法 (2016)
  • Inventor(s): 熊谷直哉、野田秀俊、古舘 信、朝田康子、柴﨑正勝
  • Industrial Property Rights Holder: 公益財団法人微生物化学研究会
  • Industrial Property Rights Type: 特許
  • Filing Date: 2016-11-23
  • Overseas