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菅 博幸  スガ ヒロユキ

教員組織学術研究院(工学系)電話番号
教育組織工学部 物質化学科FAX番号
職名教授メールアドレス
住所ホームページURLhttp://www.chem.shinshu-u.ac.jp/~suga/

更新日:2023/07/28

プロフィール

兼担研究科・学部
大学院理工学系研究科
大学院総合工学系研究科
研究分野
有機化学
有機合成化学
キーワード:複素環化合物 , 付加環化反応 , 分子触媒 , 合成化学
現在の研究課題
複素環化合物の合成及び合成化学的利用

立体選択的反応の開発と合成化学的応用

分子触媒を用いる新規エナンチオ選択的反応の開発

触媒的不斉1,3-双極性付加環化反応の開発

所属学会
所属学会
日本化学会
アメリカ化学会
有機合成化学協会
International Society of Heterocyclic Chemestry
学歴
出身大学院
1988 , 九州大学 , 総合理工学研究科
1985 , 九州大学 , 総合理工学研究科

出身学校・専攻等(大学院を除く)
1983 , 山口大学 , 工学部

取得学位
工学博士 , 九州大学
研究職歴等
研究職歴
2006- , 信州大学 教授
1998- , 信州大学 助手
1998- , 信州大学 助教授
1996- , 大阪大学大学院 (理学研究科) 助手
1994- , 大阪大学 (理学部) 助手
1988- , 九州大学 教務員
1988- , 大阪大学 (教養部) 助手

留学歴
1996- , ミシガン大学

研究活動業績

研究業績(著書・
発表論文等)
書籍等出版物
Methods and Applications of Cycloaddition Reactions in Organic Syntheses, 175-204
John Wiley & Sons 2014
Author:Manabu ABE, Haruyasu ASAHARA, Ramil Y. BAIAZITOV, Scott BUR, Pauline CHIU, Steven D. R. CHRISTIE, Hervé CLAVIER, Jun DENG, Scott E. DENMARK, Francesco De SARLO, James DOUGLAS, Xu-Fei FU, Michael HARMATA, Richard P. HSUNG, Kennosuke ITOH, Darin E. JONES, Akio KAMIMURA, Chitoshi KITAMURA, Kensuke KIYOKAWA, Sarah Y. Y. LAM, Fabrizio MACHETTI, Satoshi MINAKATA, Louis C. MORRILL, *Nagatoshi NISHIWAKI, Albert PADWA, Hélène PELLISSIER, Edward RICHMOND, Andrew D. SMITH, Takahiro SOETA, Hiroyuki SUGA, Ryukichi TAKAGI, Kiyosei TAKASU, Youhei TAKEDA, Osamu TAMURA, Yutaka UKAJI, Hidemitsu UNO, Xiao-Na WANG, Hayley T. A. WATSON, Yosuke YAMAOKA, Zhi-Xiang YU


論文
多機能な分子性触媒を志向したホスホニウムイリドの創製
有機合成化学協会誌,81(4):333-340 2023
Author:戸田泰徳,菅 博幸


Visible-Light-Driven C-H Imidation of Arenes and Heteroarenes by a Phosphonium Ylide Organophotoredox Catalyst: Application to C-H Functionalization of Alkenes
J. Org. Chem.,88(13):9574-9578 2023
Author:Yasunori Toda, Toya Kobayashi, Fumiya Hirai, Takamichi Yano, Makoto Oikawa, Kimiya Sukegawa, Masahiro Shimizu, Fuyuki Ito, Hiroyuki Suga


Ring-fused hexahydro-1,2,4,5-tetrazines: synthesis, structure, and mechanistic studies on isolable rotational isomers
Chem. Commun.,59(6):700-703 2023
Author:Yasunori Toda, Airi Kooguchi, Kimiya Sukegawa, Ayaka Kikuchi, Hiroyuki Suga


Asymmetric Cycloadditions of Acyclic Carbonyl Ylides with Aldehydes Catalyzed by a Chiral Binaphthyldiimine-Ni(II) Complex: Enantioselective Synthesis of 1,3-Dioxolanes and Mechanistic Studies by DFT Calculations
Org. Lett.,24(26):4739-4744 2022
Author:Yasunori Toda, Kayo Sato, Kensuke Sato, Kazuma Nagasaki, Hirotaka Nakajima, Ayaka Kikuchi, Kimiya Sukegawa, Hiroyuki Suga


Switchable synthesis of cyclic carbamates by carbon dioxide fixation at atmospheric pressure
ROYAL SOC CHEMISTRY,57(54):6672-6675 2021
Author:Yasunori Toda, Minoru Shishido, Tatsuya Aoki, Kimiya Sukegawa, Hiroyuki Suga


Enantioselective Protonation of Cyclic Carbonyl Ylides by Chiral Lewis Acid Assisted Alcohols
Chem. Eur. J.,27(41):10578-10582 2021
Author:Yasunori Toda, Takayuki Yoshida, Kaoru Arisue, Kazuaki Fukushima, Hiroyoshi Esaki, Ayaka Kikuchi, Hiroyuki Suga


A phosphonium ylide as a visible light organophotoredox catalyst: A mechanistic study
Chem. Commun.,57(19):3591-3594 2021
Author:Yasunori Toda, Katsumi Tanaka, Riki Matsuda, Tomoyuki Sakamoto, Shiho Katsumi, Masahiro Shimizu, Fuyuki Ito, Hiroyuki Suga


Synthesis of 1,2,5-oxadiazinane derivatives by photochemical cycloaddition of nitrones with diaminomethanes
ChemPhotoChem,4(6):388-392 2020
Author:Kennosuke Itoh, Atsushi Takashino, Atsushi Ohtsuka, Mizuki Kobe, Shunsuke Sawamura, Ryo Kato, Shigeto Hirayama, Fumika Karaki, Takaaki Mizuguchi, Noriko Sato, Ken Tokunaga, Yasunori Toda, Hiroyuki Suga, Hitoshi Ishida, Hideaki Fujii


A phosphonium ylide as a ligand for [3 + 2] coupling reactions of epoxides with heterocumulenes under mild conditions
J. Org. Chem.,85(16):10980-10987 2020
Author:Yasunori Toda, Kousuke Hashimoto, Yoko Mori, Hiroyuki Suga


Methoxy groups increase reactivity of bifunctional tetraarylphosphonium salt catalysts for carbon dioxide fixation: A mechanistic study
J. Org. Chem.,84(23):15578-15589 2019
Author:Yasunori Toda, Yutaka Komiyama, Hiroyoshi Esaki, Kazuaki Fukushima, Hiroyuki Suga


Visible-light-triggered catalytic halohydrin synthesis from epoxides and trichloroacetonitrile by copper and iron salts
Chem. Lett.,48(12):1469-1471 2019
Author:Yasunori Toda, Katsumi Tanaka, Riki Matsuda, Hiroyuki Suga


4-Hydroxymethyl-substituted Oxazolidinone Synthesis by Tetraarylphosphonium salt-catalyzed Reactions of Glycidols with Isocyanates
Chem. Commun.,55(41):5761-5764 2019
Author:Yasunori TODA, Shoya TANAKA, Shuto GOMYOU, Ayaka KIKUCHI, Hiroyuki SUGA


Novel Asymmetric Photodimerization Reaction of Coumarin Derivatives Bearing a Chiral 2-Oxazolidinone Auxiliary
RSC Adv.,9(22):12365-12369 2019
Author:Kennosuke ITOH, Fumiya ODATE, Takuma KARIKOMI, Keishi OBE, Tsutomu MIYAMORI, Hideaki KAMIYA, Kenji YOZA, Kenichiro NAGAI, Hideaki FUJII, Hiroyuki SUGA, Ken TOKUNAGA


Use of Trichloroacetonitrile as a Hydrogen Chloride Generator for Ring-opening Reactions of Aziridines
Org. Biomol. Chem.,17(15):3825-3829 2019
Author:Yasunori TODA, Riki MATSUDA, Shuto GOMYOU, Hiroyuki SUGA


Enantioselective Synthesis of 8-Azabicyclo[3.2.1]octanes via Asymmetric 1,3-Dipolar Cycloadditions of Cyclic Azomethine Ylides Using a Dual Catalytic System
Chem. Commun.,55(11):1552-1555 2019
Author:Hiroyuki SUGA, Masahiro YOSHIWARA, Takaaki YAMAGUCHI, Takashi BANDO, Mizuki TAGUCHI, Ayano INABA, Yuichi GOTO, Ayaka KiKUCHI, Kennosuke ITOH, Yasunori TODA


Lewis Acid Catalysis in Intermolecular [2+2] Photocycloaddition of Coumarin-3-carboxamide Bearing 2-Oxazolidinone Auxiliary with n-Propyl Vinyl Ether and Vinyl Pivalate
Heterocycles,97(1):591-603 2018
Author:Kennosuke ITOH, Junya MATSUURA, Hideaki KAMIYA, Ryuki KUDO, Yuki TAKAHASHI, Yuta HASHIMOTO, Kenji YOZA, Ken TOKUNAGA, Hideaki FUJII, Hiroyuki SUGA


Enantioselective Cycloadditions between Aliphatic Nitrile Oxides and 2-Hydroxystyrenes Catalyzed by Chiral Amine-urea
Heterocycles,97(1):147-150 2018
Author:Yasunori TODA, Masato KOYAMA, Hiroyoshi ESAKI, Kazuaki FUKUSHIMA, Hiroyuki SUGA


Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8-Oxabicyclo[3.2.1]octane Frameworks
Adv. Synth. Catal.,360(12):2377-2381 2018
Author:Yasunori TODA, Masahiro SHIMIZU, Taichi IWAI, Hiroyuki SUGA


Three-Component Reactions of Diazoesters, Aldehydes, and Imines Using a Dual Catalytic System Consisting of a Rhodium(II) Complex and a Lewis Acid
Org. Lett.,20(9):2659-2662 2018
Author:Yasunori TODA, Wakatake KAKU, Makoto TSURUOKA, Sho SHINOGAKI, Tomoka ABE, Hideaki KAMIYA, Ayaka KIKUCHI, Kennosuke ITOH, Hiroyuki SUGA


Efficient Generation of an Oxidopyrylium Ylide Using a Pd Catalyst and Its [5+2] Cycloadditions with Several Dipolarophiles
Chem. Commun.,54(9):1109-1112 2018
Author:Hiroyuki Suga, Taichi Iwai, Masahiro Shimizu, Kie Takahashi, Yasunori Toda


Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides
Org. Lett.,19(21):5786-5789 2017
Author:Yasunori Toda, Shuto Gomyou, Shoya Tanaka, Yutaka Komiyama, Ayaka Kikuchi, Hiroyuki Suga


A Phosphonium Ylide as an Ionic Nucleophilic Catalyst for Primary Hydroxyl Group Selective Acylation of Diols
ACS Catal.,7(9):6150-6154 2017
Author:Yasunori Toda, Tomoyuki Sakamoto, Yutaka Komiyama, Ayaka Kikuchi, Hiroyuki Suga


Amine‐Urea‐Mediated Asymmetric Cycloadditions between Nitrile Oxides and o‐Hydroxystyrenes by Dual Activation
Angew. Chem. Int. Ed.,56(39):11936-11939 2017
Author:Hiroyuki Suga, Yohei Hashimoto, Yasunori Toda, Kazuaki Fukushima, Hiroyoshi Esaki, Ayaka Kikuchi


Tetraarylphosphonium Salt-Catalyzed Carbon Dioxide Fixation at Atmospheric Pressure for the Synthesis of Cyclic Carbonates
ACS Catalysis,6(10):6906-6910 2016
Author:Yasunori Toda, Yutaka Komiyama, Ayaka Kikuchi, and Hiroyuki Suga


Photochemically-induced C–C Bond Formation between Tertiary Amines and Nitrones
Org. Biomol. Chem.,13(33):8919-8924 2015
Author:Kennosuke ITOH, Ryo KATO, Daito KINUGAWA, Hideaki KAMIYA, Ryuki KUDO, Masayuki HASEGAWA, Hideaki FUJIIA, Hiroyuki SUGA


Chiral Lewis Acid-Catalyzed Enantioselective Cycloadditions between Indoles and Cyclic Carbonyl Ylides Derived from Diazodiketone or Diazoketoester Derivatives
J. Org. Chem.,80(13):6687-6696 2015
Author:Hiroyuki SUGA, Yurie SEKIKAWA, Shunta MISAWA, Daito KINUGAWA, Rinnosuke ODA, Kennosuke ITOH, Yasunori TODA, Ryotaro KIYONO


Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Carbonyl Ylides Generated from Diazoimide Derivatives and their Synthetic Applications to Indolizidine Alkaloids
J. Org. Chem.,78(21):10840-10852 2013
Author:Hiroyuki SUGA, Yuta HASHIMOTO, Shingo YASUMURA, Ryota TAKEZAWA


Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid−Carbonyl Reaction−Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions
J. Org. Chem.,78(12):6182-6195 2013
Author:Yuta HASHIMOTO, Kennosuke ITOH, Akikazu KAKEHI, Motoo SHIRO, Hiroyuki SUGA


Novel Rearrangements of a 8aH-Pyrido[1,2-d]thieno[2’,3’-b][1,4]thiazepine Derivative
Heterocycles,85(2):305-312 2012
Author:Akikazu KAKEHI, Kennosuke ITOH, Hiroyuki SUGA, Yuuki OHKUBO, Ayaka KOBAYASHI, Takashi NISHI


Molecular Recognition of 2-(Arylmethylthio)indolizine Derivatives Through an Intramolecular Aene-(cation) Interaction
Heterocycles,84(2):753-764 2012
Author:Akikazu KAKEHI, Kennosuke ITOH, Hiroyuki SUGA, Nobuhiro YAMAGUCHI, Takashi ABE, Yohei YUDA, Haruka KATSUMATA


Asymmetric Cycloaddition Reactions of Diazoesters with 2-Alkenoic Acid Derivatives Catalyzed by Binaphthyldiimine Ni(II) complexes
J. Org. Chem.,76(18):7377–7387 2011
Author:Hiroyuki SUGA, Yasuhisa FURIHATA, Atsushi SAKAMOTO, Kennosuke ITOH, Yukihisa OKUMURA, Teruko TSUCHIDA, Akikazu KAKEHI, Toshihide BABA


Unexpected Formation of Thiino[3’,4’:4,5]oxazolo[1,3-b][1,3]oxazepine Derivatives
Heterocycles,83(3):1013-1016 2011
Author:Akikazu KAKEHI, Kennosuke ITOH, Hiroyuki SUGA, Hirofumi KOBAYASHI, Hideyuki MURANAKA


A New Synthetic Approch to Some Functionalized Cyclo[3.2.2]azine Derivatives
Heterocycles,82(2):1251-1266 2011
Author:Hideyuki MURANAKA, Akikazu KAKEHI, Hiroyuki SUGA, Kennosuke Itoh


Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform
HETEROCYCLES,81(9):2075-2086 2010(Sep.)
Author:Abe, T.; Kakehi, A.; Suga, H.; Okumura, Y.; Itoh, K.


Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Imines with Acrolein Catalyzed by L-Proline and Its Derivatives
Heterocycles,81(7):1669-1688 2010(Jul.)
Author:Hiroyuki SUGA, Tadashi ARIKAWA, Kennosuke ITOH, Yukihisa OKUMURA, Akikazu KAKEHI, Motoo SHIRO


Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates
TETRAHEDRON,66(16):3070-3089 2010(Apr.)
Author:Suga, H; Higuchi, S; Ohtsuka, M; Ishimoto, D; Arikawa, T; Hashimoto, Y; Misawa, S; Tsuchida, T; Kakehi, A; Baba, T


PREPARATION OF NEW NITROGEN-BRIDGED HETEROCYCLES. 68. ONE-POT SYNTHSIS OF 4-SUBSTITUTED 5-ACYLTHIENO[3,2-d]THIAZOLE DERIVATIVES
HETEROCYCLES,81(1):175-184 2010(Jan.)
Author:Kakehi, A; Suga, H; Okumura, Y; Nishi, T


A New Approach to Imidazo[1,2-a]pyridine Derivatives and Their Application to the Syntheses of Novel 2H-Pyrano[2’,3’:4,5]imidazo[1,2-a]pyridin-2-one Derivatives
HETEROCYCLES,80(1):439-454 2010(Jan.)
Author:Abe, T.; Okumura, Y.; Suga, H.; Kakehi, A.


Preparation of new nitrogen-bridged heterocycles. 72. A New Approach to 1-Acyl-3-(substituted methylthio)thieno[3',4':4,5]imidazo[1,5-a]pyridine Derivatives
Chem. Pharm. Bull.,58(11):1502-1510 2010
Author:Akikazu KAKEHI, Hiroyuki SUGA, Yukihisa OKUMURA, Kennosuke ITOH, Kouji KOBAYASHI, Yoshihiro AIKAWA, Kotaro MISAWA


Preparation of New Nitrogen-bridged Heterocycles 67. Syntheses of ,’-Bis[(thieno[3,4-b]indolizin-3yl)]-o-, m-, and p-xylene Derivatives and Their Conformational Structures
Chem. Pharm. Bull.,57(12):1385-1390 2009
Author:Akikazu KAKEHI, Hiroyuki SUGA, Yukihisa OKUMURA, Masatoshi SHINOHARA, Tomonao KAKO, Takeshi SEKIGUCHI, Motoo SHIRO


First Formation of Thiepino[2,3-b]- and Thiepino[3,2-a]indolizine Derivatives
Heterocycles,78(2):319-324 2009
Author:Hidetoshi ISAWA, Hiroyuki SUGA, Akikazu KAKEHI


Preparation of New Nitrogen-bridged Heterocycles 64. A Smooth Formation of 2,4-Diarylpyrido[2,3-b]indolizine-10-carbonitrile Derivatives
Heterocycles,77(1):471-481 2009
Author:Akikazu KAKEHI, Hiroyuki SUGA, Shuichi SATO


Asymmetric 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides Catalyzed by Chiral Binaphthyldiimine-Ni(II) Complexes
J. Org. Chem.,74(3):1099-1113 2009
Author:Hiroyuki SUGA, Yuki ADACHI, Kouhei FUJIMOTO, Yasuhisa FURIHATA, Teruko TSUCHIDA, Akikazu KAKEHI, Toshihide BABA


Preparation of New Nitrogen-bridged Heterocycles 63. Unexpected Formation of Thieno[3’,4’:4,5]imidazo[1,2-a]pyridines
Heterocycles,76(1):391-399 2008
Author:Akikazu KAKEHI, Hiroyuki SUGA, Atsushi Izumida, Takashi Abe


Reaction of Potassium Pyrazolo[1,5-a]pyridine-2-thiolates with Electron-poor Alkynes
Hetreocyclic Commun.,14(3):141-148 2008
Author:Hidetoshi ISAWA, Akikazu KAKEHI, Hiroyuki SUGA


Lewis Acid-Catalyzed Michael Addition Reactions of N-Boc-2-silyloxypyrroles to 3-Acryloyl-2-oxazolidinone
Heterocycles,71(2):361-371 2007(Jan.)
Author:Suga H., Takemoto H, Kakehi A.


First ring contraction-desulfurization of 1-(arylcarbonyl)pyrido[2,1-c]-1,4-thiazines to 1-(arylcarbonyl)indolizines and its application to 3-arylthieno[3,2-a]indolizine synthesis
Heterocycles,74:521-532 2007
Author:Akikazu KAKEHI, Hiroyuki SUGA, Yuichi GOTO, Nobuhiro YAMAGUCHI


Syntheses and Conformational Analyses of Bis(indolizin-1-yl) Disulfides
Chem. Pharm. Bull.,55(10):1458-1465 2007
Author:Akikazu KAKEHI, Hiroyuki SUGA, Hiroko OKUNO, Masaki OKUHARA, Akira OHTA


Preparation of New Nitrogen-bridged Heterocycles 59. Syntheses and Intramolecular Interactions of 3-(Acylmethylthio)- and 3-[(3-Ethoxycarbonyl-2-propenyl)thio]thieno[3,4-b]indolizine Derivatives
Chem. Pharm. Bull.,55(1):95-101 2007
Author:Akikazu KAKEHI, Hiroyuki SUGA, Hirohide, ISOGAI


Dipole-LUMO/Dipolarophile-HOMO Controlled Asymmetric Cycloadditions of Carbonyl Ylides Catalyzed by Chiral Lewis Acids
Org. Lett.,9(21):4359-4362 2007
Author:Hiroyuki SUGA, Daisuke ISHIMOTO, Satoshi HIGUCHI, Motoo OHTSUKA


Highly Enantioselective and Diastereoselective 1,3-Dipolar Cycloaddition Reactions between Azomethine Imines and 3-Acryloyl-2-oxazolidinone Catalyzed by Binaphthyldiimine-Ni(II) Complexes
Org. Lett.,9(1):97-100 2007
Author:Hiroyuki SUGA, Akira FUNYU, Akikazu KAKEHI


Asymmetric cycloaddition reactions between 2-benzopyrylium-4-olates and 3-(2-alkenoyl)-2-oxazolidinones in the presence of 2,6-bis(oxazolinyl)pyridine-lanthanoid complexes
Tetrahedron,62(39):9218-9225 2006(Sep.)
Author:Suga H., Suzuki T., Inoue K., Kakehi A.


Chiral 2,6-bis (oxazolinyl)pyridine-rare earth metal complexes as catalysts for highly enantioselective 1,3-dipolar cycloaddition reactions of 2-benzopyrylium-4-olates
JOURNAL OF ORGANIC CHEMISTRY,70(1):47-56 2005
Author:Suga, H; Inoue, K; Inoue, S; Kakehi, A; Shiro, M


Highly exo-selective and enantioselective cycloaddition reactions of nitrones catalyzed by a chiral binaphthyidiimine-Ni(II) complex
ORGANIC LETTERS,7(7):1431-1434 2005
Author:Suga, H; Nakajima, T; Itoh, K; Kakehi, A


Syntheses of some 1-(alpha-hydroxybenzyl)thieno[3,4-b]indolizine derivatives and their unexpected condensation reactions
HETEROCYCLES,65(7):1557-1560 2005
Author:Kakehi, A; Suga, H; Hatayama, S; Kubo, D


Preparation of new nitrogen-bridged heterocycles. 58. - Syntheses and intramolecular arene-pi interactions of 3-(allylthio)- and 3-(propargylthio)thieno[3,4-b]indolizine derivatives
CHEMICAL & PHARMACEUTICAL BULLETIN,53(11):1430-1438 2005
Author:Kakehi, A; Suga, H; Kaneko, Y; Fujii, T; Tanaka, N


Efficient catalytic effects of Lewis acids in the 1,3-dipolar cycloaddition reactions of carbonyl ylides with imines
JOURNAL OF ORGANIC CHEMISTRY,70(26):10782-10791 2005
Author:Suga, H; Ebiura, Y; Fukushima, K; Kakehi, A; Baba, T


Chiral 2,2’-Binaphthyldiimine-nickel(II) Complexes as Lewis Acid Catalysts for Enantioselective Diels-Alder Reactions
Bull. Chem. Soc. Jpn.,77(3):561-568 2004(Mar.)
Author:Hiroyuki SUGA, Akikazu KAKEHI, Masashi MITSUDA


Preparation of new nitrogen-bridged heterocycles. 55. Reinvestigation of the bromination/dehydrobromination of ethyl 3-[2-(methylthio)indolizin-3-yl]acrylate derivatives
CHEMICAL & PHARMACEUTICAL BULLETIN,52(2):279-281 2004
Author:Kakehi, A; Ito, S; Suga, H; Kobayashi, Y; Zuo, P; Iriye, R


Asymmetric Michael addition reactions of 2-silyloxyfurans catalyzed by binaphthyldiimine-Ni(II) complexes
CHEMICAL COMMUNICATIONS,(12):1414-1415 2004
Author:Suga, H; Kitamura, T; Kakehi, A; Baba, T


Preparation of new nitrogen-bridged heterocycles. 56. Syntheses and reactions of 1-[2,2-bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium salts
CHEMICAL & PHARMACEUTICAL BULLETIN,52(11):1316-1321 2004
Author:Kakehi, A; Suga, H; Yamauchi, Y; Yasuraoka, K; Kobayashi, T; Ohta, A


Stereoselectivity in 1,3-Dipolar Cycloaddtion Reactions of 2-Benzopyrylium-4-olate with Acrylic Acid Derivatives Catalyzed by Rare Earth Metal Triflate
Synthesis,2003(9):1413-1418 2003(Sep.)
Author:Kei INOUE, Hiroyuki SUGA, Shuichi INOUE, Hiroki SATO, Akikazu KAKEHI


Enantio- and Diastereoselectivity in 1,3-Dipolar Cycloaddition Reactions of Nitrones with 3-Crotonoyl-2-oxazolidinone Catalyzed by Ni(II)-Binaphthyldiimine Complexes
Bull. Chem. Soc. Jpn.,76(2):327-334 2003(Feb.)
Author:Hiroyuki SUGA, Akikazu KAKEHI, Suketaka ITO, and Hiroaki SUGIMOTO


Asymmetric Cyclopropanation and Aziridination Reactions of Olefins Catalyzed by Cu(I)-Binaphthyldiimine Complexes
Bull. Chem. Soc. Jpn.,76(1):189-199 2003(Jan.)
Author:Hiroyuki SUGA, Akikazu KAKEHI, Suketaka ITO, Toshikazu IBATA, Tomomi FUDO, Yuzuru WATANABE, Yoshinori KINOSHITA


Preparation of new nitrogen-bridged heterocycles. 53. Syntheses of 3-(benzylthio)thieno[3,4-b]indolizine derivatives and their intramolecular arene-arene interactions
CHEMICAL & PHARMACEUTICAL BULLETIN,51(1):75-84 2003
Author:Kakehi, A; Ito, S; Suga, H; Miwa, T; Mori, T; Fujii, T; Tanaka, N; Kobayashi, T


Preparation of new nitrogen-bridged heterocycles. 54. Increased arene-arene interactions of 3-(bicyclic and tricyclic arylmethylthio)thieno[3,4-b]indolizine derivatives
CHEMICAL & PHARMACEUTICAL BULLETIN,51(11):1246-1252 2003
Author:Kakehi, A; Suga, H; Kako, T; Fujii, T; Tanaka, N; Kobayashi, T


A through-space interaction of 3-benzylthiothieno[3,4-b]indolizine derivatives combined by a highly flexible spacer
HETEROCYCLES,57(1):17-20 2002
Author:Kakehi, A; Ito, S; Suga, H; Miwa, T; Mori, T; Kobayashi, T


Highly Enantioselective 1,3-Dipolar Cycloaddition Reactions of 2-Benzopyrylium-4-olate Catalyzed by Chiral Lewis Acids
J. Am. Chem. Soc,124(50):14836-14837 2002
Author:Hiroyuki SUGA, Kei INOUE, Shuichi INOUE, Akikazu KAKEHI


Asymmetric Diels-Alder Reactions Catalyzed by Chiral Ni(II)-Binaphthyldiimine Complexes
Chem. Lett.,2002(9):900-901 2002
Author:Hiroyuki SUGA, Akikazu KAKEHI, Masashi MITSUDA


Preparation of new nitrogen-bridged heterocycles. 50. Syntheses of some heterocyclic compounds starting from pyridinium 1-(ethoxycarbonylacetyl)methylides
HETEROCYCLES,54(1):185-200 2001
Author:Kakehi, A; Ito, S; Suga, H; Yasuraoka, K


Stereocontrol in a ytterbium triflate-catalyzed 1,3-dipolar cycloaddition reaction of carbonyl ylide with N-substituted maleimides and dimethyl fumarate
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,74(6):1115-1121 2001
Author:Suga, H; Kakehi, A; Ito, S; Inoue, K; Ishida, H; Ibata, T


Preparation of new nitrogen-bridged heterocycles. 51. Syntheses and structures of compounds having two indolizine nuclei in a molecule
CHEMICAL & PHARMACEUTICAL BULLETIN,49(11):1401-1405 2001
Author:Kakehi, A; Ito, S; Suga, H; Sakurai, S; Kobayashi, T


Conformation of Polychloronitrophenyl N-Substituted Morpholines Studied by DNMR and X-Ray Crystal Structure
J. Chem. Research (S),:265 2001
Author:Xinzhou ZOU, Hiro KUMA, Toshikazu IBATA, Hiroyuki SUGA


Regioselectivity in Formal [3 + 2] Cycloaddition Reaction of 5-Alkoxyoxazoles with Diethyl Oxomalonate and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Heterocycles,55(9):1711-1725 2001
Author:Hiroyuki SUGA, Xiaolan SHI, Toahikazu IBATA, Akikazu KAKEHI


Preparation of new nitrogen-bridged heterocycles. 47. Reactions of 2-indolizinethiolates with acetylenic compounds
HETEROCYCLES,52(1):215-226 2000
Author:Kakehi, A; Ito, S; Suga, H; Takahashi, H; Dobashi, K


Stereocontrol in rare earth metal triflate-catalyzed 1,3-dipolar cycloaddition reaction of 2-benzopyrylium-4-olate with aldehydes
ORGANIC LETTERS,2(20):3145-3148 2000
Author:Suga, H; Kakehi, A; Ito, S; Inoue, K; Ishida, H; Ibata, T


Cis and enantioselective synthesis of 2-oxazoline-4-carboxylates through Lewis acid-catalyzed formal [3+2] cycloaddition of 5-alkoxyoxazoles with aldehydes
JOURNAL OF ORGANIC CHEMISTRY,64(19):7040-7047 1999
Author:Suga, H; Ikai, K; Ibata, T


Lewis acid catalyzed formal [3+2] cycloaddition of 5-alkoxyoxazoles and thiiazoles
REVIEWS ON HETEROATOM CHEMISTRY,21:195-221 1999
Author:Suga, H; Ibata, T


Enantioselective Synthesis of cis-2-Oxazoline-4-carboxylates by Lewis Acid Catalyzed Formal [3 + 2] Cycloaddition of 5-Alkoxyoxazoles with Aldehydes
Tetrahedron Lett.,39(8):869-872 1998
Author:Hiroyuki SUGA, Kosei IKAI, Toshikazu IBATA


Total Synthesis of (±)-Quinolizidine 217A
J. Org. Chem.,64(19):7040-7047 1998
Author:William H. PEARSON, Hiroyuki SUGA


Stereocontrol of metal-catalyzed cycloaddition of carbonyl ylide with N-substituted maleimide
TETRAHEDRON LETTERS,39(20):3165-3166 1998
Author:Suga, H; Ishida, H; Ibata, T


Synthesis of 2,5-dihydro-1,2,4-oxadiazoles through formal [3+2] cycloaddition of oxazoles with nitrosobenzene derivatives
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,71(5):1231-1236 1998
Author:Suga, H; Shi, XL; Ibata, T


Cu(I)-binaphthyldiimine catalyzed asymmetric cyclopropanation of olefin with diazoacetate
SYNLETT,(8):933-935 1998
Author:Suga, H; Fudo, T; Ibata, T


Preparation of new nitrogen-bridged heterocycles. 45. Smooth hydrolysis of 6-membered heterocyclic 2-imines with partial aromaticity
CHEMICAL & PHARMACEUTICAL BULLETIN,46(10):1632-1634 1998
Author:Kakehi, A; Ito, S; Suga, H; Takano, S; Hirata, K


Preparation of new nitrogen-bridged heterocycles. 46. Selective formation of 4(1H)-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)-3-(1,3-oxathiol-2-ylidene)-2(3H)-indolizinone derivatives
CHEMICAL & PHARMACEUTICAL BULLETIN,46(12):1866-1871 1998
Author:Kakehi, A; Ito, S; Suga, H; Kobayashi, T; Hatanaka, S


Regio-Selectivity and Relative Reactivity of Ylide Formation in the Reaction of Ketocarbenoid with Hetero-Cumulenes
Heterocyclic Commun.,2(1):87-90 1996
Author:Toshikazu IBATA, Motomu HIMORI, Kazuaki FUKUSHIMA, Hiroyuki SUGA, Hirofumi NAKANO


Highly Diastereoselective Synthesis of 2-Oxazoline-4-carboxylates by Formal [3 + 2] Cycloadditions of a 5-Alkoxyoxazole with -Alkoxyaldehydes Catalyzed by Tin(IV) Chloride
J. Org. Chem.,59(12):3359-3364 1994
Author:Hiroyuki SUGA, Hiroki FUJIEDA, Yoshihiro HIROTSU, Toshikazu IBATA


Regio-Control of Formal [3 + 2] Cycloadditions of 5-Alkoxyoxazoles with Diethyl Oxomalonate
Chem. Lett.,(9):1673-1676 1994
Author:Hiroyuki SUGA, Xiaolan SHI, Toshikazu IBATA


Stereoselective Synthesis of 2-Oxazoline-4-carboxylates through Lewis Acid-Catalyzed Formal [3 + 2] Cycloadditions of 5-Alkoxyoxazoles with Aldehydes
J. Org. Chem.,58(26):7397-7405 1993
Author:Hiroyuki SUGA, Xiaolan SHI, Toshikazu IBATA


Abnormal Diels-Alder Reaction of 5-Alkoxyoxazoles with Tetracyanoethylene and X-Ray Crystal Structure of an Adduct
Bull. Chem. Soc. Jpn.,65(11):1771-1778 1992
Author:Toshikazu IBATA, Yasushi ISOGAMI, Hiroyuki NAKAWA, Hatsue TAMURA, Hiroyuki SUGA, Xiaolan SHI, Hiroki FUJIEDA


Abnormal Diels-Alder Reaction of Oxazoles with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione and Diethyl Azodicarboxylate, and X-Ray Crystal Structure of an Adduct
Bull. Chem. Soc. Jpn.,65(11):2998-3007 1992
Author:Toshikazu IBATA, Hiroyuki SUGA, Yasushi ISOGAMI, Hatsue TAMURA, Xiaolan SHI


Abnormal Diels-Alder Reaction of 5-Alkoxythiazoles with Highly Reactive Dienophiles; 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione, Diethyl Azodicarboxylate, and Diethyl Oxomalonate
Bull. Chem. Soc. Jpn.,65(12):3315-3321 1992
Author:Xiaolan SHI, Toshikazu IBATA, Hiroyuki SUGA, Kiyoshi MATSUMOTO


Reaction of Oxazoles with Nitrosobenzene. A Route to 1,2,4-Oxadiazolines
Chem. Lett.,(7):1221-1224 1991
Author:Hiroyuki SUGA, Toshikazu IBATA


Reactions of 5-Alkoxyoxazoles with Aldehydes in the Presence of Lewis Acid: Regio- and Stereoselective Formation of 4-Alkoxycarbonyl-2-oxazolines
Tetrahedron Lett.,32(47):6911-6914 1991
Author:Hiroyuki SUGA, Xiaolan SHI, Hiroki FUJIEDA, Toshikazu IBATA


Synthesis of 4-[(E)-1-Alkenyl]-2-hydroxybutanolides and (Z)-4-Alkylidene-2-butenolides through Cycloadditions Using a Phosphorus-Functionalized Nitrile Oxide
Bull. Chem. Soc. Jpn.,62(1):171-179 1989
Author:Shuji KANEMASA, Norihiko NAKAGAWA, Hiroyuki SUGA, Otohiko TSUGE


Acid-Catalyzed Transformation of -Hydroxy--oxo Acetals to -Oxo Esters. A Novel Deconjugation of 4-Oxo-2-alkenal Acetals
Bull. Chem. Soc. Jpn.,62(1):180-184 1989
Author:Shuji KANEMASA, Norihiko NAKAGAWA, Hiroyuki SUGA, Otohiko TSUGE


Synthesis of 2-(1-Phosphorylalkyl)- and 2-(1-Alkenyl)furans through Nitrile Oxide Cycloaddition Route
Bull. Chem. Soc. Jpn.,61(6):2133-2146 1988
Author:Otohiko TSUGE, Shuji KANEMASA, Hiroyuki SUGA


Generation of Sulfur-Functionalized Nitrile Oxide, (Phenylthio)acetonitrile Oxide, and Synthetic Applications
Bull. Chem. Soc. Jpn.,61(11):3973-3982 1988
Author:Shuji KANEMASA, Yasumasa NORISUE, Hiroyuki SUGA, Otohiko TSUGE


An Entry to 5-(1-Alkenyl)-3(2H)-furanones through Cycloaddition of Phosphorus-Functionalized Nitrile Oxide to Acetylene Alcohols. An Effective Synthesis of Geiparvarin
Chem. Lett.,(2):323-326 1987
Author:Otohiko TSUGE, Shuji KANEMASA, Hiroyuki SUGA


Synthesis of (Diethoxyphosphoryl)acetonitrile Oxide and Its Cycloaddition to Olefins. Synthetic Applications to 3,5-Disubstituted 2-Isoxazolines
Bull. Chem. Soc. Jpn.,60(7):2463-2473 1987
Author:Otohiko TSUGE, Shuji KANEMASA, Hiroyuki SUGA, Norihiko NAKAGAWA


Horner-Emmons Olefination of 4-Hydroxy-2-oxoalkylphosphonates and Related Compounds: Applications to the Syntheses of (±)-Gingerol, (±)-Yashabushiketol, and (±)-Dihydroyashabushiketol
Bull. Chem. Soc. Jpn.,60(11):4091-4098 1987
Author:Otohiko TSUGE, Shuji KANEMASA, Norihiko NAKAGAWA, Hiroyuki SUGA


Synthesis of a New Phosphorus-Functionalized Nitrile Oxide, -(Diethylphosphono)acetonitrile Oxide, and Cycloaddition Leading to 3-(Diethylphosphonomethyl)-2-isoxazolines
Chem. Lett.,(2):183-186 1986
Author:Otohiko TSUGE, Shuji KANEMASA, Hiroyuki SUGA


A Novel Ring-Opening Reaction of Aziridine Induced by the Formation of Nitrogen-Substituted Carbanion of Nonstabilized Type
Heterocycles,22(9):1955-1958 1984
Author:Otohiko TSUGE, Shuji KANEMASA, Hiroyuki SUGA, Koyo MATSUDA

研究費
科学研究費補助金(研究代表者)
2004 - , キラルルイス酸触媒を用いるカルボニルイリドの不斉付加環化反応の開発 , 基盤研究(C)
2003 - , キラルルイス酸を用いるカルボニルイリドの不斉付加環化反応の開発 , 基盤研究(C)(一般)
2000 - , 軸不斉金属触媒存在下でのジアゾカルボニル化合物を用いる不斉反応の開発 , 基盤研究(C)
1999 - , 軸不斉金属触媒存在下でのジアゾカルボニル化合物を用いる不斉反応の開発 , 基盤研究(C)
1995 - , オキサゾールとアルデヒド類との反応による2-オキサゾリンの不斉合成 , 奨励研究(A)
1991 - , オキサゾールおよびチアゾールと電子受容性化合物との反応と合成化学への利用 , 奨励研究(A)
1989 - , 複素芳香族化合物をジエン,親双極子とする超高圧下の周辺環状付加反応 , 奨励研究(A)
2019 - 2021 , 「金属/酸」ハイブリッド触媒系における双極性化合物の立体選択的反応の開発 , 基盤研究(C)
2017 - 2019 , 計算化学的スクリーニングを利用した有機分子触媒反応の設計および開発 , 基盤研究(C)(特設分野)
2015 - 2017 , イリド活性化法を基軸とする新規立体選択的分子変換法の開拓と合成化学的応用 , 基盤研究(C)
2012 - 2014 , 架橋ヘテロ原子化合物の構築を基盤とする革新的アルカロイド不斉合成法の開拓 , 基盤研究(C)
2008 - 2010 , キラルルイス酸を触媒とする汎用性不斉双極性付加環化の開発と合成化学的応用 , 新学術領域研究
2008 - 2010 , 架橋酸素多環式化合物の汎用性不斉合成法の開拓と合成化学的応用 , 基盤研究(C)
2005 - 2006 , キラルテクノロジーを用いる触媒的生理活性複素環の合成 , 基盤研究(C)

受託事業
2002 - , 分子内アセタール誘導体の立体選択的合成とその生理活性に関する研究

教育活動実績

授業等
2018 , 前期 , 有機立体化学
2018 , 前期 , 有機化学実験
2018 , 後期 , 有機化学Ⅱ
2018 , 後期 , 有機化学演習
2018 , 後期 , 有機合成化学特論
2018 , 後期 , 一般化学Ⅱ
2018 , 通年 , 有機合成化学演習
2018 , 通年 , 有機合成化学特別実験第1
2018 , 通年 , 有機合成化学特別実験第2