Details of the Researcher

PHOTO

Yusuke Sasano
Section
Graduate School of Pharmaceutical Sciences
Job title
Associate Professor
Degree

  • 博士（薬学）（東北大学）

  • 修士（薬学）（東北大学）

Research History 6

  • 2024/08 - Present
    Tohoku University　Graduate School of Pharmaceutical Sciences

  • 2020/01 - 2024/07
    Tohoku University　Graduate School of Pharmaceutical Sciences　Lecturer

  • 2014/10 - 2019/12
    Tohoku University　Graduate School of Pharmaceutical Sciences　Assistant Professor

  • 2014/11 - 2015/11
    The Scripps Research Institute　Department of Chemistry (Prof. Ryan A. Shenvi)　Research Associate

  • 2012/04 - 2014/09
    Tohoku University　Graduate School of Pharmaceutical Sciences　Research Instructor

  • 2010/04 - 2012/03
    JSPS　Research Fellowship for Young Scientists (DC1)

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Education 3

  • Tohoku University　Graduate School of Pharmaceutical Sciences　(Prof. Yoshiharu Iwabuchi)

    2010/04 - 2012/03

  • Tohoku University　Graduate School of Pharmaceutical Sciences　(Prof. Yoshiharu Iwabuchi)

    2008/04 - 2010/03

  • Tohoku University　Faculty of Pharmaceutical Sciences　(Prof. Yoshiharu Iwabuchi)

    2004/04 - 2008/03

Committee Memberships 1

  • 次世代を担う有機化学シンポジウム　世話人

    2018/05 - Present

Professional Memberships 4

  • THE JAPANESE SOCIETY FOR PROCESS CHEMISTRY

  • THE CHEMICAL SOCIETY OF JAPAN

  • THE SOCIETY OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN

  • THE PHARMACEUTICAL SOCIETY OF JAPAN

Research Interests 3

  • Nitroxyl Radical

  • Oxidation

  • Synthetic Organic Chemistry

Research Areas 4

  • Nanotechnology/Materials / Synthetic organic chemistry /

  • Life sciences / Bioorganic chemistry /

  • Nanotechnology/Materials / Structural/physical organic chemistry /

  • Life sciences / Pharmaceuticals - chemistry and drug development /

Papers 50

  1. Colorimetric quantification of vancomycin by highly active nitroxyl radical compounds

    Kyoko Sugiyama, Fumiya Sato, Kentaro Yoshida, Sachiko Komatsu, Tetsuya Ono, Yusuke Sasano, Yoshiharu Iwabuchi, Tsutomu Fujimura, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences　41　(2)　179-183　2024/11/19

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1007/s44211-024-00686-5 　

    ISSN： 0910-6340

    eISSN： 1348-2246

  2. Oxoammonium salts exert antiviral effects against coronavirus via denaturation of their spike proteins

    Ryosuke Segawa, Yusuke Sasano, Yusuke Hatakawa, Yuto Fujisawa, Shuhei Akutsu, Masanobu Uchimura, Ami Ikura, Kota Matsumoto, Kazuki Sone, Tomoyuki Oe, Yoshiharu Iwabuchi, Masashi Ito, Noriyasu Hirasawa

    Scientific Reports　14　(1)　2024/10/13

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1038/s41598-024-75097-7 　

    eISSN： 2045-2322

  3. Controlled Aerobic Oxidative Dimerization of Hydroxystilbenoids by Chromium Catalysis

    Shota Nagasawa, Yudai Itagaki, Yusuke Sasano, Yoshiharu Iwabuchi

    Organic Letters　26　(20)　4178-4182　2024/05/10

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.orglett.4c00839 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  4. Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors

    Masaki Toda, Kyoko Sugiyama, Fumiya Sato, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Katsuhiko Sato

    Chemical and Pharmaceutical Bulletin　72　(3)　249-252　2024/03/01

    Publisher: Pharmaceutical Society of Japan

    DOI： 10.1248/cpb.c23-00710 　

    ISSN： 0009-2363

    eISSN： 1347-5223

  5. Comprehensive Structural and Electronic Properties of 2-Azaadamantane N-Oxyl Derivatives Correlated with Their Catalytic Ability Peer-reviewed

    Masaki Nishijima, Yusuke Sasano, Yoshiharu Iwabuchi, Yasuyuki Araki

    ACS Omega　8　49067-49072　2023/12/26

    DOI： 10.1021/acsomega.3c06902 　

  6. Determination of antibiotics by amperometry using nortropine N-oxyl, a highly active nitroxyl radical

    Tetsuya Ono, Fumiya Sato, Masayuki Kumano, Sachiko Komatsu, Kyoko Sugiyama, Kazuhiro Watanabe, Kentaro Yoshida, Yusuke Sasano, Tsutomu Fujimura, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences　2023/06/28

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1007/s44211-023-00388-4 　

    ISSN： 0910-6340

    eISSN： 1348-2246

  7. Asymmetric Total Synthesis of Cytotrienin A: Late-stage Installation of C11 Side Chain onto the Macrolactam Scaffold. International-journal

    Yuki Tateishi, Ryo Sato, Shingo Komatsu, Masatsugu Noguchi, Shota Nagasawa, Yusuke Sasano, Naoki Kanoh, Yoshiharu Iwabuchi

    Angewandte Chemie (International ed. in English)　e202303140　2023/05/22

    DOI： 10.1002/anie.202303140 　

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    Cytotrienin A, an ansamycin-class antibiotic, exhibits potent apoptosis-inducing activity and has attracted much attention as a lead compound for anticancer drugs. Herein, we report a new asymmetric synthetic route to cytotrienin A, employing an unexplored approach involving the late-stage installation of a C11 side chain onto the macrolactam core. In this strategy, we utilized the redox properties of hydroquinone and installed a side chain on the sterically hindered C11 hydroxyl group via the traceless Staudinger reaction. This study also demonstrated that the boron-Wittig/iterative Suzuki-Miyaura cross-coupling sequence was effective for the concise and selective construction of the (E,E,E)-conjugated triene moiety. The developed route opens new opportunities for the structure-activity relationship studies of the side chains of these ansamycin antibiotics and the preparation of other synthetic analogs and chemical probes for further biological studies.

  8. 4‐Chloro‐2‐azaadamantane N‐Oxyl (4‐Cl‐AZADO): A Readily Preparable Organocatalyst for NOx Co‐catalyzed Aerobic Alcohol Oxidation

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    Asian Journal of Organic Chemistry　12　(4)　2023/02/17

    Publisher: Wiley

    DOI： 10.1002/ajoc.202300031 　

    ISSN： 2193-5807

    eISSN： 2193-5815

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    Abstract Concise synthesis and structure‐activity relationships study of 4‐substituted 2‐azaadamantane N‐oxyls reveals that 4‐chloro‐2‐azaadamantane N‐oxyl (4‐Cl‐AZADO) is an efficient organocatalyst toward the aerobic oxidation of alcohols in the presence of NOx as a co‐catalyst. The organocatalyst was easily synthesized from 2‐adamantanone in five steps, and it showed high activity compared with many previously reported nitroxyl radical catalysts.

  9. Identification of the Optimal Framework for Nitroxyl Radical/Hydroxylamine in Copper-Cocatalyzed Aerobic Alcohol Oxidation Peer-reviewed

    Masaki Toda, Yusuke Sasano, Masaya Takahashi, Shogo Fujiki, Koki Kasabata, Tetsuya Ono, Katsuhiko Sato, Yoshitomo Kashiwagi, Yoshiharu Iwabuchi

    The Journal of Organic Chemistry　88　(3)　1434-1444　2023/02/03

    Publisher: American Chemical Society ({ACS})

    DOI： 10.1021/acs.joc.2c02327 　

    ISSN： 0022-3263 1520-6904

  10. Azetidine synthesis by La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines. International-journal

    Yuse Kuriyama, Yusuke Sasano, Yoshiharu Iwabuchi

    Frontiers in chemistry　11　1251299-1251299　2023

    DOI： 10.3389/fchem.2023.1251299 　

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    Azetidine is a prevalent structural motif found in various biologically active compounds. In this research paper, we report La(OTf)3-catalyzed intramolecular regioselective aminolysis of cis-3,4-epoxy amines to afford azetidines. This reaction proceeded in high yields even in the presence of acid-sensitive and Lewis basic functional groups.

  11. Sequential click modification of a lithium-ion endohedral fullerene connecting small molecules through a dieneazide linker

    Shogo Fujiki, Takumi Takada, Shota Nagasawa, Hiroshi Okada, Yusuke Sasano, Eunsang Kwon, Yutaka Matsuo, Yoshiharu Iwabuchi

    CHEMICAL COMMUNICATIONS　59　(9)　1237-1240　2023/01

    DOI： 10.1039/d2cc06301h 　

    ISSN： 1359-7345

    eISSN： 1364-548X

  12. Electrochemical reactions of highly active nitroxyl radicals with thiol compounds

    Masayuki Kumano, Kyoko Sugiyama, Fumiya Sato, Sachiko Komatsu, Kazuhiro Watanabe, Tetsuya Ono, Kentaro Yoshida, Yusuke Sasano, Yoshiharu Iwabuchi, Tsutomu Fujimura, Yoshitomo Kashiwagi, Katsuhiko Sato

    Analytical Sciences　2022/12/28

    Publisher: Springer Science and Business Media LLC

    DOI： 10.1007/s44211-022-00246-9 　

    ISSN： 0910-6340

    eISSN： 1348-2246

  13. Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis Peer-reviewed

    Naoki Kanoh, Yuta Terajima, Suguru Tanaka, Ryusei Terashima, Hiromichi Nishiyama, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Shinichi Nishimura, Hideaki Kakeya

    The Journal of Organic Chemistry　86　(23)　16231-16248　2021/12/03

    Publisher: American Chemical Society ({ACS})

    DOI： 10.1021/acs.joc.1c01760 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  14. Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

    Naoki Kanoh, Ryusei Terashima, Hiromichi Nishiyama, Yuta Terajima, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Hiroaki Saito, Syusuke Egoshi, Kosuke Dodo, Mikiko Sodeoka, Chengqian Pan, Yoshinobu Ikeuchi, Shinichi Nishimura, Hideaki Kakeya

    The Journal of Organic Chemistry　86　(23)　16249-16258　2021/12/03

    Publisher: American Chemical Society (ACS)

    DOI： 10.1021/acs.joc.1c01761 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  15. A chalcone derivative suppresses TSLP induction in mice and human keratinocytes through binding to BET family proteins International-journal Peer-reviewed

    Ryosuke Segawa, Hiroyuki Takeda, Takeshi Yokoyama, Momoha Ishida, Chihiro Miyata, Taiji Saito, Ryosuke Ishihara, Tomoya Nakagita, Yusuke Sasano, Naoki Kanoh, Yoshiharu Iwabuchi, Mineyuki Mizuguchi, Masahiro Hiratsuka, Noriyasu Hirasawa

    Biochemical Pharmacology　194　114819-114819　2021/12

    Publisher: Elsevier {BV}

    DOI： 10.1016/j.bcp.2021.114819 　

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    Although treatments for allergic diseases have improved, side effects and treatment resistance remain as challenges. New therapeutic drugs for allergic diseases are urgently required. Thymic stromal lymphopoietin (TSLP) is a cytokine target for prevention and treatment of allergic diseases. Since TSLP is produced from epithelial cells in allergic diseases, TSLP inhibitors may be new anti-allergic drugs. We previously identified a new inhibitor of TSLP production, named 16D10. However, its target of action remained unclarified. In this study, we found proteins binding to 16D10 from 24,000 human protein arrays by AlphaScreen-based high-throughput screening and identified bromodomain and extra-terminal (BET) family proteins as targets. We also clarified the detailed mode of interaction between 16D10 and a BET family protein using X-ray crystallography. Furthermore, we confirmed that inhibitors of BET family proteins suppressed TSLP induction and IL-33 and IL-36γ expression in both mouse and human keratinocyte cell lines. Taken together, our findings suggest that BET family proteins are involved in the suppression of TSLP production by 16D10. These proteins can contribute to the pathology of atopic dermatitis via TSLP regulation in keratinocytes and have potential as therapeutic targets in allergic diseases.

  16. Nitroxyl Radical/Copper-Catalyzed Electrooxidation of Alcohols and Amines at Low Potentials

    Kyoko Sugiyama, Yusuke Sasano, Sachiko Komatsu, Kentaro Yoshida, Tetsuya Ono, Tsutomu Fujimura, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    Chemical and Pharmaceutical Bulletin　69　(10)　1005-1009　2021/10/01

    DOI： 10.1248/cpb.c21-00409 　

    ISSN： 0009-2363

    eISSN： 1347-5223

  17. Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

    Shota Nagasawa, Shogo Fujiki, Yusuke Sasano, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY　86　(9)　6952-6968　2021/05

    DOI： 10.1021/acs.joc.1c00438 　

    ISSN： 0022-3263

    eISSN： 1520-6904

  18. Expansion of Substrate Scope for Nitroxyl Radical/Copper-Catalyzed Aerobic Oxidation of Primary Alcohols: A Guideline for Catalyst Selection

    Yusuke Sasano, Aoto Yamaichi, Ryota Sasaki, Shota Nagasawa, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN　69　(5)　488-497　2021/05

    DOI： 10.1248/cpb.c21-00043 　

    ISSN： 0009-2363

  19. Catalysis of electro-oxidation of antibiotics by nitroxyl radicals and the electrochemical sensing of vancomycin

    Tetsuya Ono, Kyoko Sugiyama, Sachiko Komatsu, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Tsutomu Fujimura, Yusuke Sasano, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi, Katsuhiko Sato

    RSC Advances　11　(35)　21622-21628　2021

    Publisher: Royal Society of Chemistry (RSC)

    DOI： 10.1039/d1ra03681e 　

    eISSN： 2046-2069

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    <p>An analytical method using nitroxyl radicals was able to quantify vancomycin (VCM) in the concentration range of 10–100 μM, which is an important concentration range for drug monitoring in blood.</p>

  20. Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3. International-journal

    Yuse Kuriyama, Yusuke Sasano, Yoshihiko Hoshino, Shun-Ichiro Uesugi, Aoto Yamaichi, Yoshiharu Iwabuchi

    Chemistry (Weinheim an der Bergstrasse, Germany)　27　(6)　1961-1965　2020/11/15

    DOI： 10.1002/chem.202004455 　

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    Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf) 3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5- endo - tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.

  21. Electrochemical Evaluation of Nitroxyl Radical Catalysts and Electrochemical Detection of Cyclosporin A

    Sachiko Komatsu, Yusuke Sasano, Kyoko Sugiyama, Kazuhiro Watanabe, Masayuki Kumano, Kentaro Yoshida, Tetsuya Ono, Yoshiharu Iwabuchi, Tsutomu Fujimura, Katsuhiko Sato, Yoshitomo Kashiwagi

    2020/10/05

    Publisher: MDPI AG

    DOI： 10.20944/preprints202010.0105.v1 　

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    Nitroxyl radical catalysts oxidize alcohols under an applied electric potential. It is possible to quantify the alcohol concentration from the resulting oxidation current. In this work, we evaluated the catalytic activity of nitroxyl radicals (or their corresponding hydroxylamines), including 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as representative nitroxyl radicals, acetoamido-TEMPO, which shows higher oxidation potential than TEMPO owing to the acetoamido group, AZADO, Nor-AZADO, and NNO as less-hindered bicyclic nitroxyl radicals, and NHPI as an N,N-diacyl-type hydroxylamine, in acetonitrile solution. TEMPO, AZADO and NNO were also evaluated for their ability to oxidize alcohols in organic solvents, and their reactivity was compared with the electrochemical response. The most active NNO was used for electrochemical detection of cyclosporin A, a drug with a hydroxyl group.

  22. Electrochemical determination of choline using nortropine-N-oxyl for a non-enzymatic system Peer-reviewed

    Yoshitomo Kashiwagi, Tetsuya Ono, Fumiya Sato, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Yusuke Sasano, Yoshiharu Iwabuchi, Katsuhiko Sato

    Sensing and Bio-Sensing Research　27　100302-100302　2020/02

    DOI： 10.1016/j.sbsr.2019.100302 　

    ISSN： 2214-1804

    eISSN： 2214-1804

  23. Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NO <inf>x</inf> Catalysis: Large-Scale Preparation of Shi's Catalyst

    Yusuke Sasano, Hikaru Sato, Shinsuke Tadokoro, Masami Kozawa, Yoshiharu Iwabuchi

    Organic Process Research and Development　23　(4)　571-577　2019/04/19

    DOI： 10.1021/acs.oprd.8b00456 　

    ISSN： 1083-6160

    eISSN： 1520-586X

  24. Electrochemical Detection of Triglycerides Based on an Enzymatic Reaction and Electrocatalytic Oxidation with Nortropine‐N‐oxyl

    Tetsuya Ono, Katsuhiko Sato, Yusuke Sasano, Kentaro Yoshida, Takenori Dairaku, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi

    Electroanalysis　31　(4)　603-606　2019/04

    Publisher: Wiley

    DOI： 10.1002/elan.201800660 　

    ISSN： 1040-0397

    eISSN： 1521-4109

  25. Electrochemical Determination of Choline Using Nortropine-N-oxyl for a Non-Enzymatic System Peer-reviewed

    Yoshitomo Kashiwagi, Tetsuya Ono, Fumiya Sato, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Yusuke Sasano, Yoshiharu Iwabuchi, Katsuhiko Sato

    Sensing and Bio-Sensing Research　2019

  26. Methyl-Selective α-Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN-AZADO or 1-Me-AZADO) Peer-reviewed

    Satoru Nakai, Takafumi Yatabe, Kosuke Suzuki, Yusuke Sasano, Yoshiharu Iwabuchi, Jun‐ya Hasegawa, Noritaka Mizuno, Kazuya Yamaguchi

    Angewandte Chemie International Edition　58　(46)　16651-16659　2019

    DOI： 10.1002/anie.201909005 　

    ISSN： 1433-7851

    eISSN： 1521-3773

  27. Ln(OTf) <inf>3</inf> -catalysed highly regioselective alcoholysis of 2,3-epoxy alcohols

    Daichi Nakamura, Yusuke Sasano, Yoshiharu Iwabuchi

    Organic and Biomolecular Chemistry　17　(14)　3581-3589　2019/01/01

    DOI： 10.1039/c8ob02448k 　

    ISSN： 1477-0520

    eISSN： 1477-0539

  28. Electrochemical Oxidation of Amines Using a Nitroxyl Radical Catalyst and the Electroanalysis of Lidocaine

    Katsuhiko Sato, Tetsuya Ono, Yusuke Sasano, Fumiya Sato, Masayuki Kumano, Kentaro Yoshida, Takenori Dairaku, Yoshiharu Iwabuchi, Yoshitomo Kashiwagi

    Catalysts　8　(12)　649-649　2018/12/10

    Publisher: MDPI AG

    DOI： 10.3390/catal8120649 　

    eISSN： 2073-4344

  29. 2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities

    Yusuke Sasano, Naoki Kogure, Shota Nagasawa, Koki Kasabata, Yoshiharu Iwabuchi

    Organic Letters　20　(19)　6104-6107　2018/10/05

    DOI： 10.1021/acs.orglett.8b02528 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  30. Stereocontrolled Construction of ABCD Tetracyclic Ring System with Vicinal All-Carbon Quaternary Stereogenic Centers of Calyciphylline A Type Alkaloids

    Yusuke Sasano, Junpei Koyama, Kaori Yoshikawa, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

    Organic Letters　20　(10)　3053-3056　2018/05/18

    Publisher: American Chemical Society

    DOI： 10.1021/acs.orglett.8b01087 　

    ISSN： 1523-7052 1523-7060

  31. Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[33.1]nonan-3-one Oximes

    Tetsuya Kuga, Yusuke Sasano, Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    Synthesis (Germany)　50　(9)　1820-1826　2018/05/02

    Publisher: Georg Thieme Verlag

    DOI： 10.1055/s-0036-1591920 　

    ISSN： 1437-210X 0039-7881

  32. CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

    Kengo Kataoka, Keiju Wachi, Xiongjie Jin, Kosuke Suzuki, Yusuke Sasano, Yoshiharu Iwabuchi, Jun-Ya Hasegawa, Noritaka Mizuno, Kazuya Yamaguchi

    Chemical Science　9　(21)　4756-4768　2018

    Publisher: Royal Society of Chemistry

    DOI： 10.1039/c8sc01410h 　

    ISSN： 2041-6539 2041-6520

  33. IBX as a catalyst for dehydration of hydroperoxides: Green entry to α,β-unsaturated ketones: Via oxygenative allylic transposition

    Tetsuya Kuga, Yusuke Sasano, Yoshiharu Iwabuchi

    Chemical Communications　54　(7)　798-801　2018

    Publisher: Royal Society of Chemistry

    DOI： 10.1039/c7cc08957k 　

    ISSN： 1364-548X 1359-7345

  34. Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent kappa-OR Agonist

    Jeremy J. Roach, Yusuke Sasano, Cullen L. Schmid, Saheem Zaidi, Vsevolod Katritch, Raymond C. Stevens, Laura M. Bohn, Ryan A. Shenvi

    ACS CENTRAL SCIENCE　3　(12)　1329-1336　2017/12

    DOI： 10.1021/acscentsci.7b00488 　

    ISSN： 2374-7943

    eISSN： 2374-7951

  35. Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (-)-Englerin A

    Keisuke Morisaki, Yusuke Sasano, Takahiro Koseki, Takuro Shibuta, Naoki Kanoh, Wen-Hua Chiou, Yoshiharu Iwabuchi

    ORGANIC LETTERS　19　(19)　5142-5145　2017/10

    DOI： 10.1021/acs.orglett.7b02428 　

    ISSN： 1523-7060

    eISSN： 1523-7052

  36. Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    CHEMISTRY-A EUROPEAN JOURNAL　23　(43)　10276-10279　2017/08

    DOI： 10.1002/chem.201702512 　

    ISSN： 0947-6539

    eISSN： 1521-3765

  37. Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts Peer-reviewed

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    SYNLETT　28　(1)　A13-A16　2017/01

    ISSN： 0936-5214

    eISSN： 1437-2096

  38. Concise, Protecting-Group-Free Synthesis of (+)-Nemonapride via Eu(OTf)(3)-Catalyzed Aminolysis of 3,4-Epoxy Alcohol

    Shun-ichiro Uesugi, Yusuke Sasano, Shogo Matsui, Naoki Kanoh, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN　65　(1)　22-24　2017/01

    DOI： 10.1248/cpb.c16-00568 　

    ISSN： 0009-2363

  39. Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION　55　(42)　13189-13194　2016/10

    DOI： 10.1002/anie.201607752 　

    ISSN： 1433-7851

    eISSN： 1521-3773

  40. Total Synthesis of the Proposed Structure of Turkiyenine

    Hisataka Kobayashi, Yusuke Sasano, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY　2016　(2)　270-273　2016/01

    DOI： 10.1002/ejoc.201501365 　

    ISSN： 1434-193X

    eISSN： 1099-0690

  41. Highly Efficient Aerobic Oxidation of Alcohols by Using Less-Hindered Nitroxyl-Radical/Copper Catalysis: Optimum Catalyst Combinations and Their Substrate Scope

    Yusuke Sasano, Naoki Kogure, Tomohiro Nishiyama, Shota Nagasawa, Yoshiharu Iwabuchi

    CHEMISTRY-AN ASIAN JOURNAL　10　(4)　1004-1009　2015/04

    DOI： 10.1002/asia.201403245 　

    ISSN： 1861-4728

    eISSN： 1861-471X

  42. Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chiral Alkoxyamines as Precatalysts: Catalyst Structure, Active Species, and Substrate Scope

    Keiichi Murakami, Yusuke Sasano, Masaki Tomizawa, Masatoshi Shibuya, Eunsang Kwon, Yoshiharu Iwabuchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　136　(50)　17591-17600　2014/12

    DOI： 10.1021/ja509766f 　

    ISSN： 0002-7863

  43. Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds

    Yusuke Sasano, Shota Nagasawa, Mai Yamazaki, Masatoshi Shibuya, Jaiwook Park, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION　53　(12)　3236-3240　2014/03

    DOI： 10.1002/anie.201309634 　

    ISSN： 1433-7851

    eISSN： 1521-3773

  44. 3-Methyl-4-oxa-5-azahomoadamantane: Alkoxyamine-Type Organocatalyst for Alcohol Oxidation

    Yusuke Sasano, Keiichi Murakami, Tomohiro Nishiyama, Eunsang Kwon, Yoshiharu Iwabuchi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION　52　(48)　12624-12627　2013/11

    DOI： 10.1002/anie.201307144 　

    ISSN： 1433-7851

    eISSN： 1521-3773

  45. C-H MODIFICATION OF 2-AZAADAMANTANE: SYNTHESIS OF C5-FUNCTIONALIZED AZADOS FOR ADVANCED USE

    Yusuke Sasano, Tomohiro Nishiyama, Masaki Tomizawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    HETEROCYCLES　87　(10)　2109-2118　2013/10

    DOI： 10.3987/COM-13-12804 　

    ISSN： 0385-5414

    eISSN： 1881-0942

  46. 光学活性なスピロアセタール構造を有機分子触媒で創る

    笹野 裕介

    ファルマシア　48　(11)　1091-1091　2012

    Publisher: 公益社団法人 日本薬学会

    DOI： 10.14894/faruawpsj.48.11_1091 　

    ISSN： 0014-8601

  47. 9-Azanoradamantane N-Oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation

    Masaki Hayashi, Yusuke Sasano, Shota Nagasawa, Masatoshi Shibuya, Yoshiharu Iwabuchi

    CHEMICAL & PHARMACEUTICAL BULLETIN　59　(12)　1570-1573　2011/12

    DOI： 10.1248/cpb.59.1570 　

    ISSN： 0009-2363

  48. Practical Preparation Methods for Highly Active Azaadamantane-Nitroxyl-Radical-Type Oxidation Catalysts

    Masatoshi Shibuya, Yusuke Sasano, Masaki Tomizawa, Toshimasa Hamada, Masami Kozawa, Noriaki Nagahama, Yoshiharu Iwabuchi

    SYNTHESIS-STUTTGART　(21)　3418-3425　2011/11

    DOI： 10.1055/s-0030-1260257 　

    ISSN： 0039-7881

  49. Highly Efficient, Organocatalytic Aerobic Alcohol Oxidation

    Masatoshi Shibuya, Yuji Osada, Yusuke Sasano, Masaki Tomizawa, Yoshiharu Iwabuchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY　133　(17)　6497-6500　2011/05

    DOI： 10.1021/ja110940c 　

    ISSN： 0002-7863

  50. An Expeditious Entry to 9-Azabicyclo[3.3.1]nonane N-Oxyl (ABNO): Another Highly Active Organocatalyst for Oxidation of Alcohols

    Masatoshi Shibuya, Masaki Tomizawa, Yusuke Sasano, Yoshiharu Iwabuchi

    JOURNAL OF ORGANIC CHEMISTRY　74　(12)　4619-4622　2009/06

    DOI： 10.1021/jo900486w 　

    ISSN： 0022-3263

Show all ︎Show first 5

Misc. 35

  1. Photosensitized Singlet Oxygen-supported Alcohol Oxidation Mediated by Nitroxyl Radical Catalyst

    西嶋政樹, 長澤翔太, 笹野裕介, 荒木保幸, 岩渕好治, 和田健彦

    日本化学会春季年会講演予稿集(Web)　103rd　2023

  2. THE UTILITY OF OXOAMMONIUM SPECIES IN ORGANIC SYNTHESIS: BEYOND ALCOHOL OXIDATION

    Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi

    Heterocycles　105　(1)　61-114　2022

    DOI： 10.3987/REV-21-SR(R)2 　

    ISSN： 0385-5414

    eISSN： 1881-0942

  3. Studies directed toward the creation of induced pluripotent small (iPS) molecules based on naturally occurring polyene macrolactams

    叶直樹, 叶直樹, 寺嶋優太, 田中卓, 寺島隆世, 西山大陸, 長澤翔太, 笹野裕介, 岩渕好治

    複素環化学討論会講演要旨集　50th　2021

  4. アンサマクロラクタム抗腫瘍活性天然物Cytotrienin Aの合成研究

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    創薬懇話会講演要旨集　2021　2021

  5. Synthetic study of the marine alkaloid chartelline C benzene analog

    永山晶子, 黒田麻由, 上杉惇一郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(Web)　141st　2021

    ISSN： 0918-9823

  6. Synthetic Study of Cytotrienin A (2)

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(Web)　141st　2021

    ISSN： 0918-9823

  7. Aerobic oxidation of primary alcohols with nitroxyl radical/copper catalysis and one-pot reaction consisting of the alcohol oxidation and Z-selective HWE Reaction

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　140th (Web)　2020

  8. Synthetic Study on Himalensines

    小山純平, 笹野裕介, 叶直樹, 岩渕好治

    万有仙台シンポジウム　31st　2020

  9. 海洋性アルカロイドchartelline Cベンゼンアナログの合成研究

    永山晶子, 黒田麻由, 上杉惇一郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　59th　2020

  10. Synthetic Study of Cytotrienin A

    建石悠貴, 佐藤亮, 小松慎吾, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　140th (Web)　2020

  11. ニトロキシルラジカル/銅触媒的な化学選択的アルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    笹野裕介, 山一蒼仁, 田中卓, 叶直樹, 岩渕好治

    有機合成シンポジウム講演要旨集　115th　2019

  12. 高度縮合多環式ユズリハアルカロイド・カリシフィリンAの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    創薬懇話会講演要旨集　2019　2019

  13. ニトロキシルラジカル/銅触媒を用いたアルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　139th　2019

  14. Cytotrienin Aの合成研究:鈴木カップリングによるトリエン単位構築の検討

    建石悠貴, 佐藤亮, 小松慎吾, 野口正嗣, 長澤翔太, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　58th　2019

  15. Synthetic Studies on (+)-Cytotrienin A, an Apoptosis Inducing Ansamycin Antibiotic

    岩渕好治, 佐藤亮, 笹野裕介, 小松慎吾, 野口正嗣, 掛谷秀昭, 長田裕之, 叶直樹

    天然有機化合物討論会講演要旨集(Web)　60th　2018

    ISSN： 2433-1856

  16. 抗腫瘍活性ユズリハアルカロイドDaphnicyclidin AのBCD環部の立体選択的合成

    岡本健寛, 笹野裕介, 川住宗生, 宮城琢, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　138th　2018

  17. ニトロキシルラジカル/銅触媒を用いたアルコール空気酸化-HWE反応によるα,β-不飽和エステルの擬ワンポット合成

    山一蒼仁, 笹野裕介, 田中卓, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　57th　2018

  18. 高度縮合多環式ユズリハアルカロイドカリシフィリンAの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    反応と合成の進歩シンポジウム講演要旨集　44th　2018

    ISSN： 0919-2123

  19. ランタニドトリフラートを触媒としたエポキシアルコールの位置選択的開環反応の最適化

    中村大地, 笹野裕介, 上杉惇一郎, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　137th　2017

  20. 抗腫瘍活性ユズリハアルカロイドDaphniyunnine Dの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　137th　2017

  21. ランタノイドトリフラートを触媒とする3,4-エポキシアルコールの位置選択的アミノリシス反応の開発と応用

    松井将吾, 笹野裕介, 上杉惇一郎, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　56th　2017

  22. 抗腫瘍活性ユズリハアルカロイド・ダフニユニン類の合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    メディシナルケミストリーシンポジウム講演要旨集　35th　2017

    ISSN： 0919-214X

  23. ビシクロ[5.3.0]デカン型キラル合成素子の開発と天然物合成への応用

    森崎敬介, 小関尊弘, 澁田拓郎, 濱直人, 笹野裕介, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム　27th　2016

  24. (-)-Fumimycinの全合成研究

    西田佳祐, 澁田拓郎, 小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　136th　2016

  25. Daphniyunnine Dの合成研究

    小山純平, 井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　55th　2016

  26. Turkiyenineの全合成研究(2)

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　136th　2016

  27. Turkiyenineの全合成研究

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　135th　2015

  28. Turkiyenine提唱構造の全合成

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    万有生命科学振興国際交流財団仙台シンポジウム　26th　2015

  29. Turkiyenine提唱構造の全合成

    小林久剛, 笹野裕介, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集　45th　2015

  30. Daphniyunnine類の合成研究

    井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会年会要旨集(CD-ROM)　134th　2014

  31. 新規ヒドロアズレン型キラル合成素子の開発とセスキテルペノイド合成への応用

    小林久剛, 市川龍之介, 小関尊弘, 笹野裕介, 叶直樹, 岩渕好治

    シンポジウム「モレキュラー・キラリティー」講演要旨集　2014　2014

    ISSN： 1881-0861

  32. Daphnicyclidin/Daphniyunnine類の全合成研究

    井口かおり, 笹野裕介, 池田周平, 望月綾香, 澁谷正俊, 叶直樹, 岩渕好治

    複素環化学討論会講演要旨集　44th　2014

  33. Daphniyunnine Dの合成研究

    井口かおり, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　52nd　2013

  34. ヒドロアズレノイド型キラル合成素子の開発とEnglerin Aの合成研究への応用

    小関尊弘, 澁田拓郎, 笹野裕介, 叶直樹, 岩渕好治

    日本薬学会東北支部大会講演要旨集　52nd　2013

  35. 高活性アルコール酸化触媒AZADOの開発と天然物合成への活用

    岩渕好治, 澁谷正俊, 富澤正樹, 山越博幸, 服部貴宗, 佐藤貴恒, 長田祐二, 笹野裕介, 村上景一, 叶直樹

    天然有機化合物討論会講演要旨集(Web)　54th　2012

    ISSN： 2433-1856

Show all ︎Show first 5

Research Projects 10

  1. Development of Chemoselective Catalytic Oxidation Accelerated by the Use of Electroanalysis and Capillary Electrophoresis-Mass Spectrometry

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Transformative Research Areas (A)

    Institution: Tohoku University

    2021/09/10 - 2026/03/31

  2. Digitalization-driven Transformative Organic Synthesis (Digi-TOS)

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Transformative Research Areas (A)

    Institution: Kyushu University

    2021/09/10 - 2026/03/31

  3. 有機ニトロキシルラジカルー遷移金属協奏触媒の機能創成を機軸とする精密有機分子構築

    岩渕 好治, 笹野 裕介, 山越 博幸, 長澤 翔太

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(B)

    Institution: 東北大学

    2022/04/01 - 2025/03/31

  4. 新規多座配位ニトロキシル／銅触媒を用いる高難度不斉アルコール空気酸化反応への挑戦

    笹野 裕介

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 基盤研究(C)

    Institution: 東北大学

    2020/04/01 - 2023/03/31

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    2年目となるR3年度は、1年目に合成した三座配位型キラルニトロキシルラジカルと四座配位型キラルニトロキシルラジカルの、不斉アルコール酸化反応における触媒活性を評価することから研究を開始した。具体的には、ラセミ体のトランス-2-フェニル-シクロヘキサノールをモデル基質として、銅塩を共触媒とする空気酸化反応条件において、酸化的速度論的光学分割反応の検討を行った。その結果、キノリンを有する三座配位型キラルニトロキシルラジカルは、フェニル基を有する二座配位型キラルニトロキシルラジカルと全く同じエナンチオ選択性を示すことが明らかとなった。この結果は、キノリン基の形成する剛直な錯体構造によるエナンチオ選択性の向上を期待したが、剛直であるためにキノリン基が銅に配位することができなかったことによるものと考察している。1年目に合成した四座配位型キラルニトロキシルラジカルも、開発済の三座配位型キラルニトロキシルラジカルより低いエナンチオ選択性を示した。 上記の結果を受けて、三座配位型キラルニトロキシルラジカルの開発は一旦中断し、四座配位型キラルニトロキシルラジカルの開発に注力した。置換基の導入位置やリンカー長、および結合部位の官能基を変更した3種の触媒を新たに合成した。合成した四座配位型キラルニトロキシルラジカルのアルコール酸化触媒活性を検討したところ、エナンチオ選択性は中程度に止まったが、興味深いことに、ビピリジルとニトロキシルラジカルを同一分子に組み込んだ四座配位型キラルニトロキシルラジカルが、ビピリジルとニトロキシルラジカル混合した場合と同等のアルコール酸化触媒活性を示した。

  5. Precise construction of organic molecules based on organonitroxyl radical-transition metal hybrid catalysts

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2019/04/01 - 2022/03/31

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    We have developed novel organo-nitroxyl radical-transition metal catalyst hybrid catalysts that enable aerobic oxidative molecular transformations under room temperature with the activation of molecular oxygen. As a result, we were able to develop reaction conditions for oxidation of vic-amino alcohols to give either the corresponding carbonyl compound or one-carbon degradated product. On the other hand, in pursuit of catalytic intramolecular phenol coupling reactions, we were able to establish a novel reaction system in which the desired intramolecular dearomatizing phenol coupling reaction proceeds by the combination of an organonitroxyl radical and a Cr-salen complex.

  6. Aerobic Asymmetric Alcohol Oxidation Using Chiral Tridentate Nitroxyl Radical/Copper Catalysis

    Sasano Yusuke

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Early-Career Scientists

    Institution: Tohoku University

    2018/04/01 - 2020/03/31

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    The oxidative kinetic resolution (OKR) of racemic secondary alcohols using asymmetric catalysts is a profitable method of choice to obtain optically active alcohols. Over the past decades, remarkable progress has been made in the OKR of racemic secondary alcohols. However, OKR with high chemoselectivity has not been reported. In this study, we have developed highly chemo- and enantioselective aerobic OKR of racemic secondary alcohols. The key catalysts are a tridentate chiral nitroxyl radical and a copper salt.

  7. Development of nitrogen-containing versatile chiral building blocks driven by novel chemoselctive catalysis

    Iwabuchi Yoshiharu

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (B)

    Institution: Tohoku University

    2016/04/01 - 2019/03/31

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    We have developed an exceptionally chemoselective aerobic alcohol oxidation using AZADO/copper catalysis, which allows the presence of oxidation-labile functional groups, e.g. unprotected amino- and divalent sulfur groups. Based on the AZADO/copper system, a chirally modified AZADO has been designed to identify chemo- and enantioselective aerobic OKR of aliphatic secondary alcohols. We have also disclosed that Ln(OTf)3 enables catalytic intramolecular aminolysis of 3,4-epoxy-1-amines to give 2-substituted 3-hydroxypyrrolidines via unprecedented 5-endo-tet mode of cyclization.

  8. Enantioselective Aerobic Alcohol Oxidation Using Chiral Ligand-Hybridized Nitroxyl Radical/Copper Catalysis

    Sasano Yusuke

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Scientific Research (C)

    Institution: Tohoku University

    2015/04/01 - 2018/03/31

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    Development of enantioselective aerobic alcohol oxidation using chiral ligand-hybridized nitroxyl radical/copper catalysis has been investigated. After evaluation of the catalytic activities of newly synthesized chiral ligand-hybridized nitroxyl radicals, we have identified highly enantioselective conditions for oxidative kinetic resolution of racemic secondary alcohols. (49% conversion, 90% ee (s value 75)). The optimum conditions tolerate various oxidation-labile functional groups, such as methoxyphenyl, aniline, and sulfide groups.

  9. Chemoselective aerobic oxidation of amino alcohols using nitroxyl radical-copper catalysis

    SASANO Yusuke

    Offer Organization: Japan Society for the Promotion of Science

    System: Grants-in-Aid for Scientific Research

    Category: Grant-in-Aid for Young Scientists (B)

    Institution: Tohoku University

    2013/04/01 - 2015/03/31

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    Highly chemoslective aerobic alcohol oxidation using nitroxyl radical-copper catalysis has been developed. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including amino alcohols, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.

  10. 電子伝達系構築を機軸とするニトロキシルラジカル触媒を用いた新規空気酸化反応の開発

    笹野 裕介

    Offer Organization: 日本学術振興会

    System: 科学研究費助成事業

    Category: 特別研究員奨励費

    Institution: 東北大学

    2010 - 2011

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    平成23年度に報告者は,2-azaadamantane N-oxyl(AZADO)類と分子状酸素をつなぐレドックスメディエーターとして銅(Cu)が有効であることを見出した。AZADO-Cu触媒システムは,一般に困難とされているアミノアルコール類からアミノカルボニル化合物類への酸化反応を空気酸化条件下に進行させた.また,銅触媒として不均一触媒である銅ナノパーティクルが使用可能であることを見出した.以下にその具体的内容を述べる. 1.AZADO-銅触媒系を用いたアミノアルコール類の空気酸化反応 報告者は[AZADO(1-3mol%),CuCl(3mol%),2,2'-bipyridyl(3mol%),4-(dimethylamino)-pyridine(6mol%),MeCN, Air(open),rt]という条件下に種々の3級アミン及び2級アミンを有する2級アルコールが効率的に対応するケトンへと変換されることを見出した.本結果は,これまで報告者が所属する研究室で見出されたAZADO-NOx系を用いるアルコール空気酸化反応の基質適用性をさらに拡張するものである.また,本条件は化学量論量の酸の添加を必要としないという点でも,申請書で示した理想的な反応条件(中性条件)に近付いた条件と言える. 2.AZADO-銅ナノパーティクル触媒系を用いたアルコール類の空気酸化反応 報告者は,AZADO(5 mol%)と銅ナノパーティクル(5mol%; 体的な構造は未公開のため割愛)を触媒として用いることで,常圧空気下に種々のベンジルアルコールが室温で,脂肪族2級アルコールが50℃で酸化されることを見出した.これは,リガンドフリーであるため反応操作の簡便化に成功しているのみならず,AZADOと分子状酸素をつなぐレドックスメディエーターとして不均一系触媒を用いることが可能であることを初めて示したという点で意義深い.

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