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Development of Sustainable Chemical Reactions Driven by Designed Cooperative Catalysts

Research Project

Project/Area Number 17H03025
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionMicrobial Chemistry Research Foundation

Principal Investigator

Kumagai Naoya  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) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000)
Fiscal Year 2019: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2018: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2017: ¥7,930,000 (Direct Cost: ¥6,100,000、Indirect Cost: ¥1,830,000)
Keywords触媒 / サステイナブル / 反応開発 / 環境調和 / 炭素炭素結合 / 光学活性 / アミド / DATB / サスティナブル / 原子効率 / 環境調和型反応 / 有機合成 / 触媒反応 / 協奏機能 / メカニズム解析
Outline of Final Research Achievements

This research program aims at the development of efficient catalytic processes for the production of high-value chemicals via an ingenious design of catalyst system. Catalytic asymmetric carbon-carbon bond-forming reactions utilizing 7-azaindoline amides has reached its completion, incorporating carbon-, nitrogen-, oxygen-, sulfur-, halogen-functionalized amides at alpha-position to provide a wide range of acyclic chiral building blocks in a highly diastereo- and enantioselective fashion. As for DATB catalysis for efficient amide production from carboxylic acids and amines, mechanistic details have been revealed by systematic kinetic and DFT studies. Further investigation identified a readily accessible new catalyst derivative that is synthesized from inexpensive materials in a 3-step column free process, which is now commercial available on a worldwide basis.

Academic Significance and Societal Importance of the Research Achievements

有機合成化学は衛生的な社会生活を営む上で必要不可欠な多くの有用化成品のデザイン・合成・生産を担う学問分野であり、我々の実生活に密着した実用性の高い学問分野である。本研究課題は、効率的な化学反応を可能にする新規触媒技術の開発が主眼であり、触媒化学における基礎研究として新知見の探索とその論理的解析を推進した。また、これら新知見は、有用化成品生産において廃棄物を副生することなくクリーンかつ効率の高い合成プロセスを提供するものであり、将来的な社会還元性も十分に見込めるものである。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (117 results)

All 2020 2019 2018 2017 Other

All Journal Article (33 results) (of which Peer Reviewed: 33 results,  Open Access: 5 results,  Acknowledgement Compliant: 1 results) Presentation (77 results) (of which Int'l Joint Research: 31 results,  Invited: 36 results) Book (1 results) Remarks (4 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Z-Enolate Geometry in the Thioamide Aldol Reaction Illuminated by the 7-Azaindoline Auxiliary2020

    • Author(s)
      Roman Pluta, Zhao Li, Naoya Kumagai*, and Masakatsu Shibasaki*
    • Journal Title

      Org. Lett.

      Volume: 22 Issue: 3 Pages: 791-794

    • DOI

      10.1021/acs.orglett.9b04120

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] (2R,3S)‐3,4,4,4‐Tetrafluorovaline: A Fluorinated Bioisostere of Isoleucine2020

    • Author(s)
      Lennart Brewitz, Hidetoshi Noda, Naoya Kumagai*, Masakatsu Shibasaki*
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2020 Issue: 11 Pages: 1745-1752

    • DOI

      10.1002/ejoc.202000109

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Introduction of a 7-aza-6-MeO-indoline auxiliary in Lewis-acid/photoredox cooperative catalysis: highly enantioselective aminomethylation of α,β-unsaturated amides2020

    • Author(s)
      Santosh K. Pagire, Naoya Kumagai* and Masakatsu Shibasaki*
    • Journal Title

      Chem. Sci.

      Volume: 2020 Issue: 20 Pages: 5168-5174

    • DOI

      10.1039/d0sc01890b

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Thirst for Enantioselectivity in Catalytic Addition of Alkylnitriles2019

    • Author(s)
      Naoya Kumagai* and Masakatsu Shibasaki*
    • Journal Title

      Chem. Lett.

      Volume: 48 Issue: 11 Pages: 1322-1327

    • DOI

      10.1246/cl.190609

    • NAID

      130007741817

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Direct Catalytic Asymmetric Addition of Acetonitrile to Aldimines2019

    • Author(s)
      Akira Saito, Naoya Kumagai*, and Masakatsu Shibasaki*
    • Journal Title

      Org. Lett.

      Volume: 21 Issue: 20 Pages: 8187-8190

    • DOI

      10.1021/acs.orglett.9b02821

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF3 Amide to Isatin Imines2019

    • Author(s)
      Yu, J.-S.; Noda, H.; Kumagai, N.; Shibasaki, M.
    • Journal Title

      Synlett

      Volume: 30 Issue: 04 Pages: 488-492

    • DOI

      10.1055/s-0037-1611642

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Achiral Trisubstituted Thioureas as Secondary Ligands to Cu(I) Catalysts: Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Imines2019

    • Author(s)
      Pandur Venkatesan Balaji, Lennart Brewitz, Naoya Kumagai,* and Masakatsu Shibasaki*
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 9 Pages: 2644-2648

    • DOI

      10.1002/anie.201812673

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of syn-Aldols with Methyl Ketone Functionality and anti-Aldol with a Thioamide2019

    • Author(s)
      Yuya Ota, Zhao Li, Naoya Kumagai,* and Masakatsu Shibasaki*
    • Journal Title

      Synlett

      Volume: 30 Issue: 05 Pages: 620-624

    • DOI

      10.1055/s-0037-1610690

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A fluorogenic C4N4 probe for azide-based labelling2019

    • Author(s)
      Noda, H.; Asada, Y.; Shibasaki, M.; Kumagai, N.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 17 Issue: 7 Pages: 1813-1816

    • DOI

      10.1039/c8ob02695e

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Neighboring Protonation Unveils Lewis Acidity in the B3NO2 Heterocycle2019

    • Author(s)
      Noda, H.; Asada, Y.; Shibasaki, M.; Kumagai, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 141 Issue: 4 Pages: 1546-1554

    • DOI

      10.1021/jacs.8b10336

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of α-Alkoxyamides to α-Fluorinated Ketones2019

    • Author(s)
      Roman Pluta, Naoya Kumagai,* and Masakatsu Shibasaki*
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 8 Pages: 2459-2463

    • DOI

      10.1002/anie.201814607

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A C4N4 Diaminopyrimidine Fluorophore2019

    • Author(s)
      Noda, H.; Asada, Y.; Maruyama, T.; Takizawa, N.; Noda, N. N.; Shibasaki, M.; Kumagai, N.
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 17 Pages: 4299-4304

    • DOI

      10.1002/chem.201900467

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] All Non-Carbon B3NO2 Exotic Heterocycle: Synthesis, Dynamics, and Catalysis2019

    • Author(s)
      Opie, C. R.; Noda, H.; Shibasaki, M.; Kumagai, N.
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 18 Pages: 4648-4653

    • DOI

      10.1002/chem.201900715

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent-Dependent Enantio-divergence in anti-Selective Catalytic Asymmetric Nitroaldol Reactions2019

    • Author(s)
      Tomoya Karasawa, Akira Saito, Naoya Kumagai*, Masakatsu Shibasaki*
    • Journal Title

      Org. Lett.

      Volume: 21 Issue: 10 Pages: 3581-3583

    • DOI

      10.1021/acs.orglett.9b00982

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients2018

    • Author(s)
      Tomoya Karasawa, Raphael Oriez, Naoya Kumagai,* and Masakatsu Shibasaki*
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 38 Pages: 12290-12295

    • DOI

      10.1021/jacs.8b08236

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bis(2-pyridyl)amides as Readily Cleavable Amides Under Cataly1c, Neutral, and Room-Temperature Conditions2018

    • Author(s)
      Shinya Adachi, Naoya Kumagai*, Masakatsu Shibasaki*
    • Journal Title

      Synlett

      Volume: 29 Issue: 03 Pages: 301-305

    • DOI

      10.1055/s-0036-1590932

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structural and Computational Investigation of Intramolecular N...H Interactions in α- and β-Fluorinated 7-Azaindoline Amides2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of Viridiofungins, Broad-Spectrum Antifungal Agents and Serine Palmitoyl Transferase Inhibitors2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Heterogeneous Heterobimetallic Catalysis Enabling Expeditious Access to CF3-Containing vic-Amino Alcohols2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conquering amide planarity: Structural distortion and its hidden reactivity2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of α-Trifluoromethylated Carbinols: A Case Study of Tertiary Propargylic Alcohols2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Direct enolization chemistry of 7-azaindoline amides: A case study of bis(tetrahydrophosphole)-type ligands2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides2018

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu/Pd Synergistic Dual Catalysis: Asymmetric a-Allylation of an a-CF3 Amide2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] α-Halo Amides as Competent Latent Enolates: DirectCatalytic Asymmetric Mannich-type Reaction2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric Exo-selective 1,3-Dipolar Cycloaddition with Nitrones2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct N-acylation of sulfoximines with carboxylic acids catalyzed by the B3NO2 heterocycle2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photocatalytic α-acylation of ethers2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct catalytic asymmetric aldol addition an α-CF3 amide to arylglyoxal hydrates2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: preparation of (R)-diethyl(1-amino-1-phenylethyl)phosphonate2017

    • 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

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 特殊ヘテロ環の化学2020

    • Author(s)
      熊谷直哉
    • Organizer
      高砂香料株式会社 平塚研究所
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] アセトニトリルを基質とするダイレクト型触媒的不斉付加反応2020

    • Author(s)
      齊藤 誠、熊谷 直哉、柴崎 正勝
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Featuring unique 7-azaindoline auxiliaries in the cooperative Lewis-acid and visible-light photocatalysis: enantioselective synthesis of γ-aminobutyramides2020

    • Author(s)
      PAGIRE Santosh Kisan、熊谷 直哉、柴崎 正勝
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Achiral Thioureas as Ancillary Ligands to Cu(I) Catalysts: Remarkable Enhancement of Stereocontrol in Direct Catalytic Asymmetric Addition of alpha-Fluoronitriles to Aldehydes2020

    • Author(s)
      パンドル バラジ、熊谷 直哉、柴崎 正勝
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 7-Azaindoline Thioamide: Unveiling the Geometry of Enolate in Direct Aldol Reaction2020

    • Author(s)
      ロマン プルタ、李 釗、熊谷 直哉、柴﨑 正勝
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Direct Catalytic Asymmteic Aldol Reaction of α-Alkoxyamides to α-Fluorineated Ketones.2019

    • Author(s)
      Roman Pluta, 熊谷直哉, 柴崎正勝
    • Organizer
      第17回次世代を担う有機化学シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Chemistry Empowered by Unique Heterocycles2019

    • Author(s)
      Naoya Kumagai
    • Organizer
      第29回光学活性シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles.2019

    • Author(s)
      Naoya Kumagai
    • Organizer
      University College London
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Enantioselective Photocatalysis with Unique 7-Azaindoline Auxiliaries Opportunities and Challenges2019

    • Author(s)
      Santosh K. Pagire, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Systematic Examination of Catalytic Amide Bond Formation by the Readily Accessible B3NO2 Heterocycle-Containing Molecule Pym-DATB2019

    • Author(s)
      Christopher R. Opie, Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai
    • Organizer
      27th International Society of Heterocyclic Chemistry Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 特殊ヘテロ環の化学2019

    • Author(s)
      熊谷直哉
    • Organizer
      静岡県立大学
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2019

    • Author(s)
      Naoya Kumagai
    • Organizer
      Otsu Conference
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Featuring New 7-Azaindolines Auxiliaries for the Enantioselective Photocatalytic Synthesis of GABA Derivatives2019

    • Author(s)
      Santosh K. Pagire,熊谷直哉,柴崎正勝
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] アセトニトリルのダイレクト型触媒的不斉付加反応2019

    • Author(s)
      齊藤誠,熊谷直哉,柴崎正勝
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 特殊ヘテロ環を駆使する触媒反応2019

    • Author(s)
      熊谷直哉
    • Organizer
      第14回プロセス化学ラウンジ 富士フィルム和光純薬湯河原研修所
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Catalytic Function Dictated by the B3NO2 Ring System2019

    • Author(s)
      Naoya Kumagai
    • Organizer
      4th International Symposium on Precisely Designed Catalysts with Customized Scaffolding Kinsho Hall in Todaiji Culture Center
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] B3NO2特殊ヘテロ環による触媒反応2019

    • Author(s)
      熊谷直哉
    • Organizer
      新学術領域研究「高難度物質変換反応の開発を指向した精密制御反応場の創出」第6回公開シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Chemistry Empowered by Unique Heterocycles2019

    • Author(s)
      Naoya Kumagai
    • Organizer
      日本化学会第99年会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Thioamide and Amide and their Applications in Enantioselective Synthesis of Natural Products2019

    • Author(s)
      Jin CUI, 竹内 倫文, 大朏 彰道, 渡辺 匠, 熊谷 直哉, 柴崎 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] α-ケトエステルのanti選択的触媒的不斉ニトロアルドール反応2019

    • Author(s)
      柄澤 智哉, Raphael ORIEZ, 熊谷 直哉, 柴﨑 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Lewis酸/光触媒系によるGABA誘導体の不斉合成法の開発2019

    • Author(s)
      Santosh Kisan PAGIRE, 熊谷 直哉, 柴﨑 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] B3NO2型ヘテロ環化合物Pym-DATBによる触媒的アミド化反応2019

    • Author(s)
      Christopher Roderick OPIE, 野田 秀俊, 柴崎 正勝, 熊谷 直哉
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 新規C4N4フルオロフォア2019

    • Author(s)
      野田 秀俊, 朝田 康子, 丸山 達朗, 滝沢 直己, 野田 展生, 柴﨑 正勝, 熊谷 直哉
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Direct Catalytic Asymmetric Aldol Reaction of Amides in the Synthesis of Fluorinated α, β-Dihydroxy Acids2019

    • Author(s)
      Roman PLUTA, 熊谷 直哉, 柴崎 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Achiral Trisubstituted Thioureas as Secondary Ligands to Cu(I) Catalysts: Direct Catalytic Asymmetric Addition of alpha-Fluoronitriles to Imines2019

    • Author(s)
      Pandur BALAJI, Lennart BREWITZ, 熊谷 直哉, 柴崎 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Direct catalytic asymmetric Mannich-type reaction of an α -CF3 amide to isatin imines supported by mechanistic study on bis(tetrahydrophosphole)-type ligands2019

    • Author(s)
      余 金生, 李 釗, 野田 秀俊, 熊谷 直哉, 柴﨑 正勝
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 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反応機構解析2018

    • Author(s)
      野田秀俊、朝田康子、柴崎正勝、熊谷直哉
    • Organizer
      第16回次世代を担う有機化学シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Catalytic Function Dictated by the B3NO2 Ring System.2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis & Catalysis
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] アミドをPlayGroundとした反応設計2018

    • Author(s)
      熊谷直哉
    • Organizer
      第29回万有仙台シンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] On the Mechanism of Direct Amidation Catalyzed by the B3NO2 Heterocyclic2018

    • Author(s)
      Hidetoshi Noda, Yasuko Asada, Masakatsu Shibasaki, Naoya Kumagai
    • Organizer
      24th IUPAC International Conference on Physical Organic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 特異ヘテロ環化合物の化学2018

    • Author(s)
      熊谷直哉
    • Organizer
      御茶の水女子大学講演
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Catalytic Function Dictated by the B3NO2 Heterocycle2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      CSJ-RSC Joint Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Edinburgh
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Nottingham
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Ludwig-Maximillians University
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Max-Planck Institute
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      ETH Zurich
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Merck Ltd., NJ, US
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Sunovion Ltd., NJ, US
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      MIT, MA, US
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Harvard University
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Caltech
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of California, Berkeley
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry Empowered by Unique Heterocycles2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Stanford University
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 希土類 /Na 異種 2 核金属触媒によるα - アミノ 3 級アルコールの迅速不斉合成と 医薬品合成への応用2018

    • Author(s)
      柄澤智哉,Raphael ORIEZ,熊谷直哉,柴﨑正勝
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Reaction Development in the Amide Playground2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      Princeton University
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reaction Development in the Amide Playground2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Michigan
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reaction Development in the Amide Playground2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      California Institute of Technology
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reaction Development in the Amide Playground2018

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Utah
    • Related Report
      2017 Annual Research Report
    • 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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Asymmetric Catalytic 1,6-Conjugate Addition of para-Quinone Methides Using 7-Azaindoline Amides2018

    • Author(s)
      孫仲冬、熊谷直哉、柴﨑正勝
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Catalytic Oligopeptide Synthesis2018

    • 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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage2018

    • 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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Direct Catalytic Asymmetric Addition of α-Aryl α-Fluoro Acetonitrile to Imines2018

    • Author(s)
      Pandur Balaji、Lennart Brewitz、熊谷直哉, 柴崎正勝
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of catalytic asymmetric C-C bond-forming reactions using alkylnitriles as pronucleophiles2017

    • Author(s)
      Shaoqan Lin, Youmei Bao, Akimichi Ohtsuki, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      2nd International Symposium on Precisely Designed Catalysts with Customized Scaffolding
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-type Reaction2017

    • 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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Reaction Development in the Amide Playground2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      Shanghai Institute of Organic Chemistry (SIOC)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] DATB Catalysis: Efficient Catalytic Direct Amidation Promoted by the B3NO2 Heterocycle2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      International Symposium on Pure and Applied Chemistry 2017 (ISPAC)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reaction Development in the Amide Playground2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Ludwig-Maximilians University Munchen
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reaction Development in the Amide Playground2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      University of Munster
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asummetric α-Allylation of α-CF3 Amide Promoted by Cu/Pd Synergistic Catalyst2017

    • Author(s)
      Akira Saito, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      The19th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis(OMCOS 19)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Direct Catalytic Aldol Reaction of α-N3 Amide for the Asymmetric Synthesis of CF3-Substituted tertiary Propargylic Alcohols2017

    • 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)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reaction Development in the Amide Playground2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      Stockholm University
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Reversible stereoselective folding/Unfolding fueled by the interplay of photoisomerism and hydrogen bonding2017

    • Author(s)
      Christopher Opie, Naoya Kumagai, Masakatsu Shibasaki
    • Organizer
      RACI National Centenary Conference 2017
    • Related Report
      2017 Annual Research Report
    • 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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Topics in Amide Chemistry2017

    • Author(s)
      Naoya Kumagai
    • Organizer
      OIST: Okinawa Institute of Science & Technology
    • Related Report
      2017 Annual Research Report
    • 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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
    • 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
    • Related Report
      2017 Annual Research Report
  • [Presentation] Catalytic Oligopeptide Synthesis2017

    • 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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Book] Designed Molecular Space in Material Science and Catalysis2018

    • Author(s)
      Naoya Kumagai (Editor Seiji Shirakawa)
    • Total Pages
      262
    • Publisher
      Springer
    • ISBN
      9789811312557
    • Related Report
      2018 Annual Research Report
  • [Remarks] 微生物化学研究会HP

    • URL

      https://www.bikaken.or.jp/laboratories/organic/summary.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 微生物化学研究会

    • URL

      https://www.bikaken.or.jp/

    • Related Report
      2018 Annual Research Report
  • [Remarks] Shibasaki Lab

    • URL

      https://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index.html

    • Related Report
      2018 Annual Research Report
  • [Remarks] 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

    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report
  • [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
    • Related Report
      2017 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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