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Kazunobu Igawa Last modified date:2019.06.25

Assistant Professor / Design of Functional Organic Molecules
Department of Applied Molecular Chemistry
Institute for Materials Chemistry and Engineering


Graduate School
Undergraduate School


E-Mail
Homepage
http://www.cm.kyushu-u.ac.jp/tomooka/
Phone
092-583-7809
Fax
092-583-7810
Academic Degree
Doctor of Engineering
Field of Specialization
Organic Synthesis
Research
Research Interests
  • Creation of Chiral Silicon Compounds
    keyword : Chiral Silicon Compounds, Asymmetric Synthesis
    2003.04.
  • Chemistry Strained Molecules
    keyword : Asymmetric Synthesis, Planar Chirality, Click Chemistry
    2007.04.
  • Development of Novel Ozone Oxidation
    keyword : Ozone, Alkenylsilane, Polyol, Silylperoxide
    2005.04.
Academic Activities
Reports
1. 井川 和宣, 友岡 克彦, Silanecarboxylic Acids and Esters, Science of Synthesis, Thieme: Stuttgart, 2013.06.
Papers
1. Jun-ichi Hayashi, Kazuhiro Uehara, Yusuke Ano, Yuuya Kawasaki, Kazunobu Igawa, Katsuhiko Tomooka, SYNTHESIS AND STEREOCHEMICAL ANALYSIS OF DYNAMIC PLANAR CHIRAL NINE-MEMBERED DIALLYLIC AMIDE: SIGNIFICANT SUBSTITUENT EFFECT ON STEREOCHEMICAL STABILITY, Heterocycles, 10.3987/COM-18-S(F)92, 99, 2019.01.
2. Kazunobu Igawa, Daisuke Yoshihiro, Yusuke Abe, and Katsuhiko Tomooka, Enantioselective Synthesis of Silacyclopentanes, Angewandte Chemie International Edition, 10.1002/anie.201511728, 55, 5814-5818, 2016.04, A variety of functionalized silacyclopentanes were synthesized stereoselectively by highly enantioselective β-elimination of silacyclopentene oxides, followed by stereospecific transformations. The reaction mechanism of the β-elimination was elucidated by DFT calculations. The in vitro biological assay of an oxy-functionalized silacyclopentane showed substantial binding activity to a serotonin receptor protein..
3. Kouhei Machida, Yuki Yoshida, Kazunobu Igawa, Katsuhiko Tomooka, Efficient approach to medium-sized cyclic molecules containing (E)-Alkene via z to e photochemical isomerization in the presence of AgNO3-impregnated silica gel, Chemistry Letters, 10.1246/cl.170937, 47, 2, 186-188, 2018.01, Efficient synthesis of medium-sized cyclic molecules containing an (E)-alkene was performed via the highly (E)selective photochemical isomerization of the (Z)-isomer, facilitated by AgNO3-impregnated silica gel..
4. Kazunobu Igawa, Akihiro Kuroo, Daisuke Yoshihiro, Yuki Yamanaka, Katsuhiko Tomooka, Synthesis of Stereoselectively Functionalized Silacyclopentanes, Synlett, 10.1055/s-0036-1590826, 28, 18, 2445-2448, 2017.11, An efficient approach to a variety of chiral silacyclopentanes having silicon stereogenic center based on the stereospecific transformations of C4 carbon stereogenic center of silacyclopentenols by Mitsunobu reaction or Tsuji-Trost reaction has been developed. The thus obtained substitution products can be converted into novel silacyclopentane triols, amines, and carboxylic acids in stereospecific manner..
5. Kazunobu Igawa, Shin Aoyama, Yuuya Kawasaki, Takeru Kashiwagi, Yuki Seto, Runyan Ni, Naoto Mitsuda, Katsuhiko Tomooka, Thieme Chemistry Journals Awardees
Where Are They Now? One-Pot Synthesis of Versatile Buckle Units for Click Chemistry: 4,8-Diazacyclononynes (DACNs), Synlett, 10.1055/s-0036-1588839, 2017.04, Newly designed buckle units for copper-free click chemistry: 4,8-diazacyclononynes (DACNs) were efficiently synthesized with a one-pot procedure from commercially available 2-butyne-1,4-diol. The synthesized DACNs possess versatile connectors for the introduction of functional units and exhibit high click reactivity..
6. Kazunobu Igawa, Asymmetric synthesis of chiral silicon molecules and stereoselective transformations thereof, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 10.5059/yukigoseikyokaishi.75.898, 75, 9, 898-908, 2017.01, A variety of functionalized chiral silicon molecules were stereoselectively synthesized from enantio-enriched chiral silanols or chiral silacyclopentenols, which were prepared by highly enantioselective desymmetrization reactions of achiral silicon molecules. The unique reactivity, and substantial bioactivity of the synthesized chiral silicon molecules were disclosed..
7. Kazunobu Igawa, Kouhei Machida, Kyouhei Noguchi, Kazuhiro Uehara, Katsuhiko Tomooka, Synthesis and Stereochemical Analysis of Planar-Chiral (E)-4-[7]Orthocyclophene, Journal of Organic Chemistry, 10.1021/acs.joc.6b01799, 81, 23, 11587-11593, 2016.12, An efficient synthesis of (E)-4-[7]orthocyclophene (E)-1 via photochemical isomerization of (Z)-1 has been achieved. The key intermediate (Z)-1 was synthesized from commercially available 2-(hydroxymethyl)benzenepropanol (3) in five steps: (i) group-selective Mitsunobu reaction with CH2=CHCH2CH(SO2Ph)2, (ii) oxidation of alcohol, (III) olefination, (iv) RCM, and (v) removal of sulfones in an overall yield of 73%. The photochemical isomerization of (Z)-1 was efficiently performed in the presence of AgNO3-impregnated silica gel (AgNO3/SiO2). The resulting (E)-1 shows dynamic planar chirality at rt. Enantioenriched (E)-1 was prepared by the HPLC separation of enantiomers using a chiral stationary phase, and the absolute stereochemistry was determined by X-ray diffraction analysis of the Pt-coordinated crystalline derivative. The planar chirality of (E)-1 can be converted into the central chirality of carbon; e.g., the oxidation of (R)-(E)-1 using DMDO provided epoxide (8S,9S)-9 in a stereospecific manner. Furthermore, the Lewis acid-promoted reaction of (8S,9S)-9 afforded a unique tricyclic compound (8S,9S)-10 in an excellent yield and in a stereospecific manner..
8. Hirofumi Yamamoto, Maho Ueda, Naoto Yamasaki, Akiyoshi Fujii, Ikuo Sasaki, Kazunobu Igawa, Yusuke Kasai, Hiroshi Imagawa, Mugio Nishizawa, Aryl-Allene Cyclization via a Hg(OTf)(2)-Catalytic Pathway, ORGANIC LETTERS, 10.1021/acs.orglett.6b01144, 18, 12, 2864-2867, 2016.06.
9. Kazunobu Igawa, Nobumasa Ichikawa, 阿野 勇介, Keisuke Katanoda, Toshiyuki Akiyama, Masato Ito, Katsuhiko Tomooka, Catalytic Enantioselective Synthesis of Planar-Chiral Cyclic Amides Based on a Pd-Catalyzed Asymmetric Allylic Substitution Reaction, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/jacs.5b04340, 137, 23, 7294-7297, 2015.06.
10. Katsuhiko Tomooka, Shouji Miyasaka, Shogo Motomura, Kazunobu Igawa, Planar Chiral Dialkoxysilane: Introduction of Inherent Chirality and High Reactivity in Conventional Achiral Alkene, Chem. Eur. J., 10.1002/chem.201402434, 20, 7598-7602, 2014.05.
11. Kazunobu Igawa, Yuuya Kawasaki, Kosuke Nishino, Naoto Mitsuda, Katsuhiko Tomooka, Asymmetric Ozone Oxidation of Silylalkene Using a C2-Symmetrical Dialkoxysilyl Group as a Chiral Auxiliary, Chem. Eur. J., 10.1002/chem.201402996, 20, 9255-9258, 2014.05.
12. Kazunobu Igawa, Runyan Ni, Takeshi Kawabata, Katsuhiko Tomooka, Synthesis, Structural Analysis, and Reaction of 3-Aza-5-[7]orthocyclophyne, Chem. Lett., 10.1246/cl.130735, 42, 1374-1376, 2013.10.
13. Takashi Kamachi, Ken-ichi Shimizu, Daisuke Yoshihiro, Kazunobu Igawa, Katsuhiko Tomooka, Kazunari Yoshizawa, Oxidation of Silanes to Silanols on Pd Nanoparticles: H2 Desorption Accelerated by Surface Oxyge, J. Phys. Chem. C, 10.1021/jp408269s, 117, 22967-22973, 2013.10.
14. Suguru Yoshida, Kazunobu Igawa, Katsuhiko Tomooka, Nucleophilic Substitution Reaction at the Nitrogen of Arylsulfonamides with Phosphide Anion, J. Am. Chem. Soc., 10.1021/ja309642r, 134, 19358-19361, 2012.11, 今回,我々はアリールスルホンアミドに対してホスフィドアニオンを作用させると,窒素上での求核置換反応が進行することを見出した.本反応は,窒素上の変換反応として,また,アリールスルホンアミド保護の効率的な除去法として有用である..
15. Kazunobu Igawa, Daisuke Yoshihiro, Nobumasa Ichikawa, Naoto Kokan, Katsuhiko Tomooka, Catalytic Enantioselective Synthesis of Alkenylhydrosilanes, Angew. Chem. Int. Ed., 10.1002/anie.201207361, 51, 12745-12748, 2012.11, 今回,我々はキラルケイ素分子の効率的な不斉合成法としてジヒドロシランの不斉非対称化を伴うアルキンとのヒドロシリル化反応を新たに開発することに成功した..
16. Katsuhiko Tomooka, Chisato Iso, Kazuhiro Uehara, Masaki Suzuki, Rie Nishikawa-Shimono, Kazunobu Igawa, Planar-Chiral [7]Orthocyclophanes, Angew. Chem. Int. Ed., 10.1002/anie.201204484, 51, 10355-10358, 2012.09.
17. Yuuya Kawasaki, Youhei Ishikawa, Kazunobu Igawa, Katsuhiko Tomooka, Directing Group-Controlled Hydrosilylation: Regioselective Functionalization of Alkyne, J. Am. Chem. Soc., 133, 20712-20715, 2011.12, アルキンのヒドロシリル化は合成化学的に有用なアルケニルシランの合成法として優れているが,その位置選択が低いことから適用範囲が限られていた.これに対して,本研究ではアルキンの近傍にジメチルビニルシリル基を配向基として配するという新手法を開発し,ヒドロシリル化の位置選択性の高度制御に成功した..
18. Kazunobu Igawa, Naoto Kokan, and Katsuhiko Tomooka, Asymmetric Synthesis of Chiral Silacarboxylic Acids and Their Ester Derivatives, Angew. Chem. Int. Ed., 49, 728-731, 2010.01.
19. Igawa, K.; Takada, J.; Shimono, T.; Tomooka, K., Enantioselective Synthesis of Silanol, J. Am. Chem. Soc., 130, 16132-16133, 2008.12.
20. Yong-Li Zhong, Brenda Pipik, Jaemoon Lee, Yoshinori Kohmura, Shigemitsu Okada, Kazunobu Igawa, Chie Kadowaki, Akihiro Takezawa, Shinji Kato, David A. Conlon, Hua Zhou, Anthony O. King, Robert A. Reamer, Donald R. Gauthier, Jr., and David Askin, Practical Synthesis of a HIV Integrase Inhibitor, Orag. Proc. Res. Dev., 12, 1245-1252, 2008.08.
21. Kazunobu Igawa, Kyohei Sakita, Masanori Murakami, Katsuhiko Tomooka, Partial Oxydation of Alkenylsilane with Ozone: A Novel Stereoselective Approach for the Diol- and Triol-derivatives, Synthesis, 1641, 2008.02.
22. M. Murakami, K. Sakita, K. Igawa, K. Tomooka, Stereoselective Oxy-functionalization of γ-Silyl Allylic Alcohols with Ozone: A Facile Synthesis of Silyl Peroxide and Its Reactions, Organic. Lett., 8, 4023-4026, 2006.08.
23. K. Igawa, K. Tomooka, 3. γ-Silyl Group Effect in Hydroalumination and Carbolithiation of Propargylic Alcohols, Angew. Chem. Int. Ed., 45, 232-234, 2006.01.
24. K. Tomooka, M. Kikuchi, K. Igawa, M. Suzuki, P.-H. Keong and T. Nakai, Stereoselective Total Synthesis of Zaragozic Acid A based on an Acetal [1,2]-Wittig Rearrangement, Angew. Chem. Int. Ed., 39, 4502-4505, 2000.12.
25. TakahiroKawatsu, HirokiTokushima, YuyaTakedomi, TatsushiImahori, Kazunobu Igawa, Katsuhiko Tomooka, Ryo Irie, Synthesis, stereochemical characteristics, and coordination behavior of 2,2 '-binaphthyl-1,1 '-biisoquinoline as a new axially chiral bidentate ligand, ARKIVOC, 10.3998/ark.5550190.p009.069.
26. Kazunobu Igawa, Daisuke Yoshihiro, Yusuke Abe, Katsuhiko Tomooka, Enantioselective Synthesis of Silacyclopentanes, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 10.1002/anie.201511728, 55, 19, 5814-5818.
Presentations
1. Kazunobu Igawa, Stereoselective Synthesis of Asymmetric Silicon Molecules, IRCCS The 2nd International Symposium, 2019.01.
2. Kazunobu Igawa, Daisuke Yoshihiro, Akihiro Kuroo, Yusuke Abe, Katsuhiko Tomooka, Asymmetric Synthesis of Silacyclopentanes based on Enantioselective β-Elimination of Silacyclopentene Oxide, 第6回 日英触媒的不斉合成シンポジウム, 2018.11.
3. Jun-ichi Hayashi, Yusuke Ano, Kazuhiro Uehara, Kazunobu Igawa, Katsuhiko Tomooka, Design and Synthesis of Novel Dynamic Planar-Chiral Amide: Stereochemical Effect of C4-Substituent, The 7th Junior International Conference on Cutting-Edge Organic Chemistry in Asia, 2017.10.
4. 河崎 悠也, 西野 浩輔, 光田 直人, 井川 和宣, 友岡 克彦, Asymmetric Ozone Oxidation of Silylalkene Using Chiral Silyl Auxiliary, Molecular Chirality Asia 2016, 2016.04.
5. 井川 和宣, 高田 純子, 吉廣 大佑, 古閑 直人, 安部 雄介, 友岡 克彦, Divergent Asymmetric Synthesis of Chiral Organosilanes: Enantioselective Synthesis of Chiral Silanols and Stereospecific Transformations Thereof, Molecular Chirality Asia 2016 , 2016.04.
6. Kazunobu Igawa, Reaction Control Using Silyl-substituent Effects: Synthesis of Silylalkenes and Their Ozone Oxidation, The First Asian Conference for "MONODUKURI" Strategy by Synthetic Organic Chemistry, 2013.07.
7. 井川 和宣, 河崎悠也, 村上正徳, 崎田恭平, 石川洋平, 友岡 克彦, Significant Silyl Substituent Effect on Ozone Oxidation: A Novel Approach to Multi-oxy-functionalized Compounds from Alkynes, The 4th Asian Silicon Symposium, 2012.10.
Membership in Academic Society
  • The Society of Silicon Chemistry Japan
  • The Society of Synthetic Organic Chemistry, Japan
  • The Chemical Society of Japan
Awards
  • Synthesis and Application of Novel Organosilanes
  • Chemistry of Organosilane possessing Unique Reactivity and Stereochemical Feature