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Researcher Information

last modified:2024/01/08

Professor MATSUO Junichi

Mail Laboratory Website

Faculty, Affiliation

Faculty of Pharmacy, Institute of Medical, Pharmaceutical and Health Sciences

College and School Educational Field

Division of Frontier Engineering, Graduate School of Natural Science and Technology
Division of Natural System, Graduate School of Natural Science and Technology
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences

Laboratory

Synthetic Organic Chemistry TEL:076-234-4439 FAX:076-234-4439

Academic Background

【Academic background(Doctoral/Master's Degree)】
The University of Tokyo Doctor Graduate School, Division of Pharmaceutical Sciences 199903 Completed
【Academic background(Bachelor's Degree)】
The University of Tokyo 199403
【Degree】
Ph.D.

Career

Japan Science and Technology Agency Researcher(1999/04/01-2000/03/31)
Tokyo University of Science Assistant Professor(2000/04/01-2002/03/31)
Kitasato Institute Resercher(2002/04/01-2005/08/31)
Kanazawa University(2005/09/01-)

Year & Month of Birth

1971/11

Academic Society

Award

○BCSJ Award(2002/02)
○Incentive Award in Synthetic Organic Chemistry(2004/02)
○Ninomiya Award(2004/11)
○The Pharmaceutical Society of Japan Award for Young Scientists(2008/03)
○Daiichi-Sankyo Award in Synthetic Organic Chemisry(2009/02)

Specialities

Chemical pharmacy

Speciality Keywords

Organic Reactions, Organic Synthesis

Research Themes

Development of New Organic Reactions

Total Synthesis of Bioactive Compounds

Books

Papers

  •  Enantioselective alpha-Alkylation of Phenylacetic Acid Using a Chiral Bidentate Lithium Amide as a Chiral Auxiliary Kenji Koga CHEMICAL & PHARMACEUTICAL BULLETIN 45  2122-2124 1997
  •  Enantioselective Alkyaltion of Lactams and Lactones via Lithium Enolate Formation Using a Chiral Tetradentate Lithium Amide in the Presence of Lithium Bromide ShuKobayashi, Kenji Koga TETRAHEDRON LETTERS 39  9723-9726 1998
  •  A Novel Chiral PentamineLigand for Enantioselective alpha-Alkylation of Acyclic Lithium Amide Enolates. Optimization of Chiral Ligands for Asymmetric Reactions Using Solid-Phase Organic Synthesis Kazunori Odashima, Shu Kobayashi ORGANIC LETTERS 1  345-348 1999
  •  Lewis Acid Catalyst in Supercritical Carbon Dioxide. Use of Scandium Tris(heptadecafluorooctanesulfonate) as a Lewis Acid Catalyst in Diels-Alder and Aza Diels-Alder Reactions Takehiro Tsuchiya, Kazurori Odashima, and Shu Kobayashi CHEMISTRY LETTERS 178-179 2000
  •  Gallium Nonafluorobutanesulfonate as an Efficient Catalyst in Friedel-Crafts Acylation Kazunori Odashima, and Shu Kobayashi SYNLETT 403-405 2000

show all

  •  Lithium Tetrakis(pentafluorophenyl)borate-Catalyzed Friedel-Crafts Benzylation Reactions Teruaki Mukaiyama, Masakazu Nakano, Wataru Kikuchi CHEMISTRY LETTERS 1010-1011 2000
  •  A New and Efficient Method for Oxidation of Various Alcohols by Using N-tert-Butylphenylsulfinimidoyl Chloride Jun-ichi Matsuo, and Manabu Yanagisawa CHEMISTRY LETTERS 1072-1073 2000
  •  Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates Atsushi Kawada, Shuichi Mitamura, Takehiro Tsuchiya, and Shu Kobayashi BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 73 2325-2333 2000
  •  Aldol Reaction of Enol Esters Catalyzed by Cationic Species Paired with Tetrakis(pentafluorophenyl)barate Manabu Yanagisawa, T. Shimamura, Daisuke Iida, and Teruaki Mukaiyama CHEMICAL & PHARMACEUTICAL BULLETIN 48 1838-1840 2000
  •  A New and One-Pot Synthesis of alpha,beta-Unsaturated Ketones by Dehydrogenation of Various Ketones with N-tert-Butyl Phenylsulfinimidoyl Chloride Teruaki Mukaiyama, and Hideo Kitagawa CHEMISTRY LETTERS 1250-1251 2000
  •  Aromatic iodination with iodine monochloride by using a catalytic amount of ferrocenium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate Teruaki Mukaiyama, Hideo Kitagawa TETRAHEDRON LETTERS 41 9383-9386 2000
  •  Benzylation of Alcholic Hydroxyl Groups with Benzyl Mesylate by Using a Catalytic Amount of Lithium Tetrakis(pentafluorophenyl)borate in the Coexistence of Lithium Triflate and Magnesium Oxide Masakazu Nakano, and Teruaki Mukaiyama CHEMISTRY LETTERS 1352-1353 2000
  •  A Mild and Efficient Oxidation of Alcohols with N-tert-Butylphenylsulfinimidoyl Chloride in the Coexistence of Zinc Oxide Hideo Kitagawa, Daisuke Iida, and Teruaki Mukaiyama CHEMISTRY LETTERS 150-151 2001
  •  Catalytic Friedel-Crafts Acylation of Aniline Derivatives Shu Kobayashi, Ichiro Komoto ADVANCED SYNTHESIS & CATALYSIS 343 71-74 2001
  •  Oxidation of Various Secondary Amines to Imines with N-tert-Butylphenylsulfinimidoyl Chloride Teruaki Mukaiyama, Asahi Kawana, Yoshio Fukuda CHEMISTRY LETTERS 390-391 2001
  •  An Efficient Method for the p-Methoxybenzylation of Hydroxy Groups with 2-(4-methoxybenzyloxy)-3-nitropyridine Masakazu Nakano, Wataru Kikuchi, and Teruaki Mukaiyama CHEMISTRY LETTERS 424-425 2001
  •  Oxidation of Primary Alkyl Triflates to the Corresponding Aldehydes via Alkoxy(N-tert-butylamino)(methyl)sulfonium Triflates Hideo Kitagawa, Daisuke Iida, and Teruaki Mukaiyama CHEMISTRY LETTERS 580-581 2001
  •  Oxidative Deamination of Various Primary Amines to the Corresponding Carbonyl Compounds by Using N-tert-Butylphenylsulfinimidoyl Chloride Asahi Kawana, Yoshio Fukuda, and Teruaki Mukaiyama CHEMISTRY LETTERS 712-713 2001
  •  Catalytic Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds with N-Chlorosuccinimide Using a Catalytic Amount of Sulfenamide Teruaki Mukaiyama, Daisuke Iida, and Hideo Kitagawa CHEMISTRY LETTERS 846-847 2001
  •  A convenient method for the synthesis of nitrones by oxidation of N,N-disubstituted hydroxylamines with N-t-butylbenzenesulfinimidoyl chloride Tsuyoshi Shibata, Hideo Kitagawa, and Teruaki Mukaiyama ARKIVOC 58-65 2001
  •  Scandium Perfluoroalkanesulfonate-Catalyzed Diels-Alder Reactions in an Organic Solvent Shu Kobayashi, Takehiro Tsuchiya, Ichiro Komoto JOURNAL OF ORGANOMETALLIC CHEMISTRY 624 392-394 2001
  •  A New Method for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds by Using N-t-Butylbenzenesulfinimidoyl Chloride Daisuke Iida, Kazuya Tatani, and Teruaki Mukaiyama BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 75 223-234 2002
  •  Polymer-supported Sulfinimidoyl Chloride as a Useful Reagent for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds Asahi Kawana, Khanitha Pudhom, and Teruaki Mukaiyama CHEMISTRY LETTERS 250-251 2002
  •  Efficient Method for the Preparation of Aromatic Bromides and Iodides by Ferrocenium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate-Catalyzed Halogenation with Bromine and Iodine Monochloride Hideo Kitagawa, Tsuyoshi Shibata, and Teruaki Mukaiyama BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 75 339-345 2002
  •  Catalytic Friedel-Crafts Acylation of Heteroaromatics Ichiro Komoto, Shu Kobayashi TOPICS IN CATALYSIS 19 43-47 2002
  •  Trimethylaluminum-promoted 1,4-Addition Reaction of Cuprates to Six or Eight-membered Cyclic 2-Hydroxylmethyl Enones Khanitha Pudhom, and Teruaki Mukaiyama HETEROCYCLES 59 445-451 2003
  •  N-t-Butylbenzenesulfenamide-catalyzed Oxidation of Alcohols to the Corresponding Carbonyl Compounds with N-Chlorosuccinimide Daisuke Iida, and Teruaki Mukaiyama TETRAHEDRON 59 6739-6750 2003
  •  Sulfenamide-catalyzed Oxidation of Primary and Secondary Alcohols with Molecular Bromine Asahi Kawana, Hiroyuki Yamanaka, and Teruaki Mukaiyama CHEMISTRY LETTERS 32 182-183 2003
  •  A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts Hiroyuki Yamanaka, Asahi Kawana, and Teruaki Mukaiyama CHEMISTRY LETTERS 32 392-393 2003
  •  Polymer-supported Sulfinimidoyl Chlorides: A Convenient Reagent for Oxidation of Alcohols Asahi Kawana, Hiroyuki Yamanaka, and Hiroaki Kamiyama BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 76 1433-1440 2003
  •  A Convenient Method for the Synthesis of beta,gamma-Unsaturated Amines from Alkenes via alpha,beta-Unsaturated Diphenylsulfonium Salts Hiroyuki Yamanaka, Asahi Kawana, and Teruaki Mukaiyama CHEMISTRY LETTERS 32 626-627 2003
  •  New Methods for the Preparations of 2-Arylaziridines, alpha-imidostyrenes, and allylamines from olefins via diphenylvinylsulfonium Triflates Hiroyuki Yamanaka, Asahi Kawana, and Teruaki Mukaiyama ARKIVOC 42-65 2004
  •  A Facile One-pot Benzylation of Sodium Enolates Using Trifluoromethansulfonic Anhydride and Diphenyl Sulfoxide Tomofumi Takuwa, Jim Yoshitaka Onishi, and Teruaki Mukaiyama CHEMISTRY LETTERS 33 8-9 2004
  •  Stereoselective Construction of BC-ring unit of 19-Hydroxytaxol by Samarium(II) Iodide-mediated Double Aldol Cyclizations Yasuyuki Ogawa, Khanitha Pudhom, and T. Mukaiyama CHEMISTRY LETTERS 33 124-125 2004
  •  Synthesis of cis-2-Fluorocyclopropylamine by Stereoselective Cyclopropanation Under Phase-transfer Conditions Yu-ichirou Tani, and Yu-ichirou Hayakawa CHEMISTRY LETTERS 33 464-467 2004
  •  Stereoselective Synthesis of 19-Hydroxytaxoid Using Intramolecular Pinacol Coupling Reaction Teruaki Mukaiyama, Yasuyuki Ogawa, Kiichi Kuroda, CHEMISTRY LETTERS 33 1412-1413 2004
  •  One-pot dehydrogenation of carboxylic acid derivatives to alpha,beta-unsaturated carbonyl compounds under mild conditions Yayoi Aizawa TETRAHEDRON LETTERS 46 407-410 2005
  •  Stereoselective Synthesis of 19-Hydroxytaxoid by Utilizing Samarium(II) Iodide-Mediated Double Aldol Cyclization Yasuyuki Ogawa, Kiichi Kuroda, and Teruaki Mukaiyama BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 78 677-697 2005
  •  One-pot beta-substitution of enones with alkyl groups to beta-alkyl enones Yayoi Aizawa CHEMICAL COMMUNICATIONS 2399-2401 2005
  •  Catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate Tatsuya Shirahata, and Satoshi Omura TETRAHEDRON LETTERS 47 267-271 2006
  •  Radical Cyclizations of N-Allylic or N-vinylic alpha,alpha,alpha-Trichloroacetamides in 1,4-Dimethylpiperazine Hiroyuki Ishibashi, Shigeki Haruki, Masahiko Uchiyama, Osamu Tamura TETRAHEDRON LETTERS 47 6263-6266 2006
  •  A mild and convenient synthesis of N-carbobenzyloxy ketimines Yumi Tanaki, Aimi Kido and Hiroyuki Ishibashi CHEMICAL COMMUNICATIONS 2896-2898 2006
  •  Stereoselective Synthesis of trans-3a-Aryloctahydro-indoles Using Cyclization of N-Vinylic alpha-(Methylthio)acetamides Miho Saito, Masahiko Uchiyama, and Hiroyuki Ishibashi HETEROCYCLES 68 69-72 2006
  •  Oxidative Mannich Reaction of N-Carbobenzyloxy Amines with 1,3-Dicarbonyl Compounds Yumi Tanaki, Hiroyuki Ishibashi ORGANIC LETTERS 8 4371-4374 2006
  •  Mild preparation of alkenes from phenyl sulfides: one-pot elimination of phenylthio group via sulfilimine at ambient temperature Takaaki Kozai, and Hiroyuki Ishibashi ORGANIC LETTERS 8 6095-6098 2006
  •  One-pot oxidative Mannich-type reaction of lactams with alkyl malonates Yumi Tanaki, and Hiroyuki Ishibashi TETRAHEDRON LETTERS 48 3233-3236 2007
  •  One-pot carbon-carbon bond formation at the beta-position of cyclic ketones: oxidative Michael addition with alkyl malonates Hiroki Kawai, and Hiroyuki Ishibashi TETRAHEDRON LETTERS 48 3155-3158 2007
  •  Stereoselective synthesis of cis and trans-fused 3a-aryloctahydroindoles using cyclization of N-vinylic alpha-(methylthio)acetamides: synthesis of (-)-mesembrane Miho Saito, and Hiroyuki Ishibashi TETRAHEDRON 63 4865-4873 2007
  •  A practical synthesis of enantiopure N-carbobenzyloxy-N'-phthaloyl-cis-1,2-cyclohexanediamine by asymmetric reductive amination and the Curtius rearrangement Masahiko Okano, Kosuke Takeuchi, Hiroyuki Tanaka and Hiroyuki Ishibashi TETRAHEDRON-ASYMMETRY 18 1906-1910 2007
  •  Synthesis of 13a-methylphenanthroindolizidines using radical cascade cyclization: synthetic studies towards (rac)-hypoestestatin 1 Kosuke Takeuchi, Atsuko Ishita, and Hiroyuki Ishibashi TETRAHEDRON 63 11101-11107 2007
  •  One-pot oxidative carbon-carbon bond formation of 3-benzylic and 3-allylic indoles with carbon nucleophiles Yumi Tanaki and Hiroyuki Ishibashi TETRAHEDRON 64 5262-5267 2008
  •  Oxazaborolidine-catalyzed enantioselective reduction of alpha-methylene ketones to allylic alcohols Takaaki Kozai, Osamu Nishikawa, Yu Hattori and Hiroyuki Ishibashi JOURNAL OF ORGANIC CHEMISTRY 73 6902-6904 2008
  •  Lewis Acid-Catalyzed Intermolecular [4+2] Cycloaddition of 3-Alkoxycyclobutanones to Aldehydes and Ketones Shun Sasaki, Hiroyuki Tanaka, and Hiroyuki Ishibashi JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130 11600-11601 2008
  •  Stereocontrolled Formal Synthesis of (rac)-Platensimycin Kosuke Takeuchi, and Hiroyuki Ishibashi ORGANIC LETTERS 10 4049-4052 2008
  •  Diels-Alder reaction of eight-membered cyclic siloxydienes Shun Sasaki, Takaya Hoshikawa, and Hiroyuki Ishibashi TETRAHEDRON 64 11224-11229 2008
  •  Asymmetric Synthesis of 2-alkyl-4-hydroxycyclohex-2-en-1-one by scandium(III) triflate-catalyzed fragmentation of chiral 2-alkyl-3-iodo-1-oxocyclohexan-2,4-carbolactone Mizuki Kawano, Kosuke Takeuchi, Hiroyuki Tanaka, and Hiroyuki Ishibashi TETRAHEDRON LETTERS 50 1917-1919 2009
  •  Tin(IV) Chloride-Catalyzed Cycloaddition Reactions Between 3-Ethoxycyclobutanones and Allylsilanes Shun Sasaki, Takaya Hoshikawa, and Hiroyuki Ishibashi ORGANIC LETTERS 11 3822-3825 2009
  •  Formal [4 + 2] cycloaddition between 3-ethoxycyclobutanones and silyl enol ethers Shoko Negishi, and Hiroyuki Ishibashi TETRAHEDRON LETTERS 50 5831-5833 2009

Conference Presentations

Others

  •  New Oxidations Using Sulfinimidoyl Chlorides 62 574-583 2004

Arts and Fieldwork

Patent

Theme to the desired joint research

Grant-in-Aid for Scientific Research

○「窒素‐硫黄結合を活用する新しい酸化剤による実用的酸化反応の開発」(2001-)
○「ヘテロ環を含むスルフィンイミドイルクロリドを用いる新しい有機合成反応の開発」(2002-)
○「19-ヒドロキシタキソールのタキソールの不斉全合成研究」(2004-)
○「窒素―硫黄結合の特性を活用する実用的合成反応の開発」(2007-)
○「1,4-双極性活性種を用いる新しい環化付加反応の開発と生理活性物質合成への応用」(2009-)
○「1,4-双極性活性種を用いる新しい環化付加反応の開発と生理活性物質合成への応用」(2009-2011) 
○「新しい1,4-双極性活性種を用いる合成反応の開発」(2012-2014) 

Competitive research funding,Contribution

Collaborative research,Consignment study

○Asymmetric oxidation of 24-oxocholesterol(2006-2009)

Classes (Bachelors)

○Lecture on Life in Campus and Society(2017)
○Introduction to Information Technology(2017)
○Experiments in Organic Chemistry(2017)
○Freshman Seminar I(2017)
○Organic Chemistry 3(2017)
○Seminar in Organic Chemistry 3(2017)
○Introduction to Information Technology(2016)
○Experiments in Organic Chemistry(2016)
○Freshman Seminar I(2016)
○Medicinal Chemistry(2016)
○Seminar in Organic Chemistry 3(2016)
○Laboratory Rotation 1(2016)
○Organic Chemistry 3(2016)

Classes (Graduate Schools)

○Advanced Organic Chemistry I(2017)
○Advanced Seminar on Pharmachemistry(2017)
○Introduction to Advanced Organic Chemistry(2017)
○Advanced Organic Chemistry III(2017)
○Advanced Course of Pharmachemistry(2017)
○Advanced Organic Chemistry II(2017)
○New Reactions for Organic Synthesis(2016)
○Advanced Organic Chemistry III(2016)

International Project

International Students

Lecture themes

Others (Social Activities)

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