Grant-in-Aid for Scientific Research on Innovative AreasPrecise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions

Yoshiharu Iwabuchi » Japanese

Affiliation Graduate School of Pharmaceutical Sciences, Tohoku University
Position Professor
Contact Email
Speciality Synthetic Organic Chemistry, Bioorganic Chemistry
Keyword organocatalysis, cooperative cartalysis, alcohol oxidation, asymmetric synthesis, natural product synthesis
Institute The Pharmaceutical Society of Japan, The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan, The Japanese Society for Process Chemistry, The American Chemical Society, Japanese Cancer Association

Abstract

Development of highly chemoseletive aerobic alcohol oxidation system based on AZADO-Cu cooperative catalysis

Achievement

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Original papers

  • "Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi’s Catalyst"
    Sasano, Y.; Sato, H.; Tadokoro, S.; Kozawa, M.; *Iwabuchi, Y.
    Organic Process Research & Development, 2019, 23, in press
  • "2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities"
    Sasano, Y.; Kogure, N.; Nagasawa, S.; Kasabata, K.; *Iwabuchi, Y.
    Organic Letters, 2018, 20, 6104-6104
  • "CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides"
    Kataoka, K.; Wachi, K.; *Jin, X.; Suzuki, K.; Sasano, Y.; Iwabuchi, Y.; Hasegawa, J.; Mizuno N.; *Yamaguchi, K.
    Chem. Sci., 2018, 9, 4756-4768
  • "CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides"
    Kataoka, K.; Wachi, K., *Jin, X.; Suzuki, K.; Sasano, Y.; Iwabuchi, Y.; Hasegawa, J.; Mizuno, N.; *Yamaguchi, K.
    Chem. Sci., 2018, 9, 4756-4768
  • "Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes"
    Kuga, T.; Sasano, Y.; Tomizawa, M.; Shibuya, M.; *Iwabuchi, Y.
    Synthesis, 2018, 50, in press
  • "IBX as a catalyst for dehydration of hydroperoxides: green entry to a,b-unsaturated ketones via oxygenative allylic transposition"
    Kuga, T.; Sasano, Y.; *Iwabuchi, Y.
    Chem. Comm., 2018, 54, 798-801
  • "Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (-)-Englerin A"
    Morisaki, K.; Sasano, Y.; Koseki, T.; Shibuta, T.; Kano, N.; Chou, W.-H.; *Iwabuchi, Y.
    Org, Lett., 2017, 19, 5142-5145
  • "A Mild Two-Step Propargylation of Aromatic Bioactive Small Molecules"
    Nano, N.: Okamura, T.; Suzuki, T.; Iwabuchi, Y.
    Org. Biomol. Chem., 2017, 15, 7190-7195
  • "Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst"
    Nagasawa, S.; Sasano, Y.; Iwabuchi, Y.
    Chem. Eur. J., 2017, 23(43), 10276-10279
  • "Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)3-Catalyzed Aminolysis of 3,4-Epoxy Alcohol"
    Uesugi, S.; Sasano, Y.; Matsui, S.; Kanoh, N.; Iwabuchi, Y.
    Chem. Pharm. Bull., 2017, 65,22-24
  • "Reversibility of thia-Michael reaction of the cytotoxic C5-curcuminoid and structure-activity relationship of the bis-thiol- adducts thereof"
    Kohyama, A.; Fukuda, M.; Sugiyama, S.; Yamakoshi, H.; Kanoh, N.; Ishioka, C.; Shibata, H.; Iwabuchi, Y.
    Org. Biomol. Chem. , 2016, 14, 10683-10687
  • "Design and synthesis of the penta(acetoxymethyl) ester of dioctanoyl phosphatidylinositol-3,5-bisphosphate"
    Kanoh, N.; Mano, K.; Saigusa, D.; Usui, T.; Iwabuchi, Y.
    Bioorg. Med. Chem. Lett. , 2016, 26, 5770-5772
  • "Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented reactivity of Oxoammonium Salts"
    Nagasawa, S.: Sasano, Y.; Iwabuchi, Y.
    Angew. Chem. Int. Ed. , 2016, 55, 13189-13194

Conference

  • International Congress on Pure & Applied Chemistry 2018
    "Chemoselective and Environmentally Benign Alcohol Oxidation Using Nitroxyl Radical/Copper Cooperative Catalysis", Invited Lecture
    Sasano, Y.; Kogure, N.; Nagasawa, S. Kasabata, K.; Iwabuchi, Y.
    3/7/2018~3/10/2018, Siem Reap, Cambodia
  • 2017 International Symposium on Recent Advances in Drug Discovery and Development
    "Highly Chemoselective Aerobic Alcohol Oxidation using AZADO-Copper Catalysis", Invited Lecture
    Iwabuchi, Y.
    12/8/2017~12/8/2017, Cheongju, Korea
  • The 12th International Conference on Cutting-Edge Organic Chemistry in Asia
    "Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Discovery and Exploitation of Unprecedented Reactivity of Oxoammonium Salts", Poster Presentation
    Iwabuchi, Y.; Nagasawa, S.; Sasano, Y.
    11/2/2017~11/5/2017, Xi'an, China
  • The 7th Junior International Conference on Cutting-Edge Organic Chemistry in Asia
    "Highly Chemoselective Aerobic Alcohol Oxidation Using AZADO-Copper Catalysis", Keynote Lecture
    Iwabuchi, Y.
    10/30/2017~11/1/2017, Lanzhou, China
  • The 7th Sino-Japanese Symposium on Organic Chemistry for Round Scientists
    "Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts", Invited Lecture
    Iwabuchi.¥, Y.
    10/8/2017~10/11/2017, Shanghai, China
  • 26th French-Japanese Symposium on Medicinal and Fine Chemistry
    "Development of Bicycle[5.3.0]decane-type Chiral Building Block and Its Application to Formal Total Synthesis of (-)-Englerin A", Poster Presentation
    Iwabuchi, Y.; Morisaki, K.; Takahiro, K.; Sasano, Y.; Kano, N.
    9/17/2017~9/20/2017, Strasbourg, France
  • International Symposium on Pure & Applied Chemistry
    "Highly Chemoselective Aerobic Alcohol Oxidation using AZADO-Copper Catalysis", Invited Lecture
    Iwabuchi, Y.
    6/8/2017~6/10/2017, Ho Chi Minh City, Vietnam
  • The 11th International Conference on Cutting-Edge Organic Chemistry in Asia
    "Development of Bicycle[5.3.0]decne-type Chiral Building Block and Total Synthesis of (–)-Englerin A", Poster Presentation
    Iwabuchi, Y.; Morisaki, K.; Koseki, T.; Shibuta, T.; Sasano, Y.; Naoki, K.
    10/27/2016~10/30/2016, Daejeon, Korea
  • The 3rd Symposium if SPU Innovative Project for Pharmaceutical Analyses of Covalent Modification in Biomolecules
    "Reversibility of thia-Michael reaction of the cytotoxic C5-curcuminoid GO-Y030 and structure-activity relationship of the bis-thiol-adducts thereof", Keynote Lecture
    Iwabuchi, Y.
    8/31/2016~9/1/2016, Tokyo, Japan
  • The International Symposium on Homogeneous Catalysis (ISHC XX)
    "AZADO-CuCl/bpy/DMAP/Air Enables Highly Efficient Oxidation of Amino Alcohols to Amino Carbonyl Compounds", Poster Presentation
    Iwabuchi, Y.; Sasano, Y.; Nagasawa, S.; Kogure, N.; Shibuya, M.
    7/10/2016~7/15/2016, Kyoto, Japan
  • The 25th French-Japanese Symposium on Medicinal and Fine Chemistry
    "AZADO-Cu/bpy/DMAP/Air Enables highly Chemoselective Oxidation of Amino Alcohols to Amino Carbonyl Compounds", Poster Presentation
    Iwabuchi, Y.; Sasano, Y.; Nagasawa, S.; Kogure, N.; Shibuya, M.
    5/15/2016~5/18/2016, Tokyo, Japan

National Conference

  • 日本薬学会第138回年会
    "三座配位型キラルAZADO/銅触媒系を用いたラセミ第二級アルコールの空気酸化的速度論的光学分割反応(OKR)の開発", 口頭発表
    笠畑 洸希、笹野 裕介、小暮 直貴、岩渕 好治
    3/25/2018~3/28/2018, 金沢市
  • 日本化学会 第98春季年会 (2018)
    "不斉配位子複合型ニトロキシルラジカル/銅協奏触媒を用いるラセミ第2級アルコールの酸化的速度論的光学分割に関する理論的研究", 口頭発表
    *川島恭平、笹野裕介、小暮直貴、笠畑洸希、岩渕好治、森聖治
    3/20/2018~3/23/2018, 船橋市
  • 第10回有機触媒シンポジウム
    "N,N-ジメチルアミノアダマンタンを触媒とするKornblum-DeLaMare転位反応:発見と反応機構解析", ポスター発表
    久我哲也、笹野裕介、真鍋周平、内山真伸、岩渕好治
    11/30/2017~12/1/2017, 仙台市
  • 第43回反応と合成の進歩シンポジウム
    "不斉配位子複合型ニトロキシルラジカル/銅協働触媒を用いるラセミ第2級アルコール の酸化的速度論的光学分割", ポスター発表
    *笹野裕介,小暮直貴,笠畑洸希,西山智弘,川島恭平,森聖治,岩渕好治
    11/6/2017~11/7/2017, 富山市
  • The 67th Conference of Japan Society of Coordination Chemistry
    "Aerobic Oxidation Catalyzed by Mononuclear Non-heme Iron Complexes", ポスター発表
    Takebayashi, H.; Sakai, R.; Morikawa, N.; Hiramatsu, M.; Kodera, M.; Sasano, Y.; Iwabuchi, Y.; Hitomi, Y.
    9/16/2017~9/18/2017, Sapporo
  • 第64回有機金属化学討論会
    "ニトロキシルラジカル/銅協働触媒を用いる高化学選択的アルコール空気酸化反応", ポスター発表
    *笹野裕介・長澤翔太・小暮直貴・Jaiwook Park・岩渕好治
    9/7/2017~9/9/2017, 仙台市
  • 第28回万有シンポジウム
    "ニトロキシルラジカル/銅協働触媒を用いる高化学選択的アルコール空気酸化反応:条件最適化と基質適用性拡張", ポスター発表
    *笹野 裕介、小暮 直貴、長澤 翔太、笠畑 洸希、岩渕 好治
    6/24/2017~6/24/2017, 仙台市
  • 日本薬学会第137年会
    "AZADO/Cu触媒系を用いた含硫黄アルコールの高化学選択的空気酸化反応の開発", 口頭発表
    小暮直貴、長澤翔太、笹野裕介、岩渕好治
    3/25/2017~3/27/2017, 仙台
  • 日本薬学会第137年会
    "脂肪族およびフェノール性水酸基に対する金属カルベノイドの官能基位置選択的挿入反応の開発", 口頭発表
    村上弘晃、叶直樹、岩渕好治
    3/25/2017~3/27/2017, 仙台
  • 第58回天然有機化合物討論会
    "ビシクロ[5.3.0]デカン型キラル合成素子の開発と(–)-englerin Aの全合成", 口頭発表
    森崎敬介、小関尊弘、澁田拓郎、笹野裕介、叶直樹、岩渕好治
    9/14/2016~9/16/2016, 仙台

Media

  • Chem. Sci., カバーピクチャ
    「CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides」
    Kataoka, K.; Wachi, K., *Jin, X.; Suzuki, K.; Sasano, Y.; Iwabuchi, Y.; Hasegawa, J.; Mizuno, N.; *Yamaguchi, K., 5/7/2018
    PDF File

outreach

  • 小・中・高向け授業・実験・実習
    岩渕好治, 講師, 東北大学工学部大講義室
    仙台市, 2/17/2018~2/17/2018