Development of Chiral Bronsted Acid Catalyst

• Project Area: Advanced Molecular Transformations by Organocatalysts
• Project/Area Number: 23105003
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Gakushuin University
• Principal Investigator: AKIYAMA TAKAHIKO 学習院大学, 理学部, 教授 (60202553)
• Project Period (FY): 2011-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥80,860,000 (Direct Cost: ¥62,200,000、Indirect Cost: ¥18,660,000); Fiscal Year 2015: ¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000); Fiscal Year 2014: ¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000); Fiscal Year 2013: ¥19,500,000 (Direct Cost: ¥15,000,000、Indirect Cost: ¥4,500,000); Fiscal Year 2012: ¥13,520,000 (Direct Cost: ¥10,400,000、Indirect Cost: ¥3,120,000); Fiscal Year 2011: ¥10,920,000 (Direct Cost: ¥8,400,000、Indirect Cost: ¥2,520,000)
• Keywords: 有機分子触媒 / 選択的合成 / 不斉合成 / 触媒反応 / 光学分割 / 有機合成化学 / 不斉還元反応 / ケトイミン / Friedel-Crafts反応 / 速度論的光学分割 / アトロプ異性体 / リン酸 / NMR / 触媒設計 / ベンゾチアゾリン

Outline of Final Research Achievements

Because enantiomers may exhibit different biological activities, development of novel chiral catalyst and efficient asymmetric reactions for the preparation of optically active compounds is an important topic of research interest. We already reported that chiral phosphoric acid derived from (R)-BINOL exhibited efficient catalytic activity as a chiral Bronsted acid. We tried to extend the utility of the chiral phosphoric acid and found several interesting asymmetric reactions.

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Research Products

• [Journal Article] Enantiodivergent Atroposelective Synthesis of Chiral Biaryls by Asymmetric Transfer Hydrogenation: Chiral Phosphoric Acid Catalyzed Dynamic Kinetic Resolution (2016)
  • Author(s): Keiji Mori, Tsubasa Itakura, Takahiko Akiyama
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 38 Pages: 11642-11646
  • DOI: 10.1002/anie.201606063
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] mmunication Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid (2016)
  • Author(s): Kosaku Horiguchi, Eri Yamamoto, Kodai Saito, Masahiro Yamanaka, Takahiko Akiyama
  • Journal Title: Chem. Eur. J. Volume: 22 Issue: 24 Pages: 8078-8083
  • DOI: 10.1002/chem.201601611
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Chiral Phosphoric Acid Catalyzed Kinetic Resolution of Indolines Based on a Self-Redox Reaction (2016)
  • Author(s): Kodai Saito, Takahiko Akiyams
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 9 Pages: 3148-3152
  • DOI: 10.1002/anie.201510692
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines (2015)
  • Author(s): Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama
  • Journal Title: Chem. Commun. Volume: 51 Issue: 93 Pages: 16648-16651
  • DOI: 10.1039/c5cc06436h
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Stronger Bronsted Acids: Recent Progress (2015)
  • Author(s): Keiji Mori, Takahiko Akiyama
  • Journal Title: Chem. Rev. Volume: 115 Issue: 17 Pages: 9277-9306
  • DOI: 10.1021/acs.chemrev.5b00041
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of 2-Substituted 2,3-Dihydro-4-quinolones by a Protecting-Group-Free Approach (2015)
  • Author(s): Kodai Saito, Yuka Moriya, Takahiko Akiyama
  • Journal Title: Org. Lett. Volume: 17 Issue: 13 Pages: 3202-3205
  • DOI: 10.1021/acs.orglett.5b01654
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Benzothiazoline: Versatile Hydrogen Donor for Organocatalytic Transfer Hydrogenation (2015)
  • Author(s): Chen Zhu, Kodai Saito, Masahiro Yamanaka, Takahiko Akiyama
  • Journal Title: Acc. Chem. Res. Volume: 48 Issue: 2 Pages: 388-398
  • DOI: 10.1021/ar500414x
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Enantioselective Synthesis of Chiral Biaryl Chlorides/Iodides by a Chiral Phosphoric Acid Catalyzed Sequential Halogenation Strategy (2015)
  • Author(s): Keiji Mori, Manato Kobayashi, Tsubasa Itakura, Takahiko Akiyama
  • Journal Title: Adv. Synth. Catal. Volume: 357 Issue: 1 Pages: 35-40
  • DOI: 10.1002/adsc.201400611
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Enantioselective Fluorination of β-Ketoesters Catalyzed by Chiral Sodium Phosphate : Remarkable Enhancement of Reactivity by Simultaneous Utilization of Metal Enolate and Metal Phosphate (2014)
  • Author(s): Mori, K.; Miyake, A.; Akiyama, T
  • Journal Title: Chem. Lett Volume: 43 Issue: 1 Pages: 137-139
  • DOI: 10.1246/cl.130934
  • NAID: 130004427102
  • Peer Reviewed
• [Journal Article] Stereoselective Construction of All Carbon Quaternary Center by Means of Chiral Phosphoric Acid : Highly Enantioselective Friedel-Crafts Reaction of Indoles with β,β-Disubstituted Nitoroalkenes (2014)
  • Author(s): Mori, K.; Wakazawa, M.; Akiyama, T
  • Journal Title: Chem. Sci Volume: 5 Issue: 5 Pages: 1799-1803
  • DOI: 10.1039/c3sc53542h
  • Peer Reviewed
• [Journal Article] Chiral Phosphoric-Acid-Catalyzed Transfer Hydrogenation of Ethyl Ketimine Derivatives by Using Benzothiazoline (2014)
  • Author(s): Saito, K.; Horiguchi, K.; Shibata, Y.; Yamanaka, M.; Akiyama, T.
  • Journal Title: Chem. Eur. J. Volume: 20 Issue: 25 Pages: 7616-7620
  • DOI: 10.1002/chem.201402763
  • Peer Reviewed
• [Journal Article] Asymmetric Transfer Hydrogenation of Ketimines by Indoline as Recyclable Hydrogen Donor (2014)
  • Author(s): Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama
  • Journal Title: Org. Lett. Volume: 16 Issue: 20 Pages: 5312-5315
  • DOI: 10.1021/ol502486f
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Phosphoric Acid Bridged Cobalt Bis(dicarbollide) Ion as a Highly Efficient Catalyst for the Organocatalytic Hydrogenation of Ketimines (2014)
  • Author(s): Takahiko Akiyama, Kodai Saito, Slawomir Janczak, Zbigniew J. Lesnikowski
  • Journal Title: Synlett Volume: 25 Issue: 06 Pages: 795-798
  • DOI: 10.1055/s-0033-1340847
  • Peer Reviewed
• [Journal Article] Enantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence (2013)
  • Author(s): Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 10 Pages: 3964-3970
  • DOI: 10.1021/ja311902f
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Prediction of suitable catalyst by 1H NMR: asymmetric synthesis of multisubstituted biaryls by chiral phosphoric acid catalyzed asymmetric bromination (2013)
  • Author(s): Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T.
  • Journal Title: Chem. Sci. Volume: 4 Issue: 11 Pages: 4235-4239
  • DOI: 10.1039/c3sc52142g
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Chiral Phosphoric Acid Catalyzed Oxidative Kinetic Resolution of Indolines Based on Transfer Hydrogenation to Imines (2013)
  • Author(s): Saito, K.; Shibata, Y.; Yamanaka, M.; Akiyama, T.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 32 Pages: 11740-11743
  • DOI: 10.1021/ja406004q
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Enantioselective Transfer Hydrogenation of Difluoromethyl Ketimines Using Benzothiazoline as a Hydrogen Donor in Combination with Chiral Phosphoric Acid (2013)
  • Author(s): Sakamoto, T.; Horiguchi, K.; Saito, K.; Mori, K.; Akiyama, T.
  • Journal Title: Asian J. Org. Chem. Volume: 2 Issue: 11 Pages: 943-946
  • DOI: 10.1002/ajoc.201300174
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Carboxyl-Tailed Benzothiazoline: A Readily Removable Hydrogen Donor for the Transfer Hydrogenation of Imines (2012)
  • Author(s): Chen Zhu
  • Journal Title: Tetrahedron Lett. Volume: 53 Issue: 4 Pages: 416-418
  • DOI: 10.1016/j.tetlet.2011.11.061
  • Peer Reviewed
• [Journal Article] Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp3)-H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine (2012)
  • Author(s): Mori, K.; Kawasaki, T.; Akiyama, T
  • Journal Title: Org. Lett Volume: 14 Issue: 6 Pages: 1436-1439
  • DOI: 10.1021/ol300180w
  • Peer Reviewed
• [Journal Article] Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor (2012)
  • Author(s): Saito, K.; Akiyama, T.
  • Journal Title: Chem. Commun Volume: 48 Issue: 38 Pages: 4573-4575
  • DOI: 10.1039/c2cc31486j
  • Peer Reviewed
• [Journal Article] Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline as a Deuterium Donor : Synthesis of Optically Active Deuterated Amines (2012)
  • Author(s): Sakamoto, T.; Mori, K.; Akiyama, T
  • Journal Title: Org. Lett Volume: 14 Issue: 13 Pages: 3312-3315
  • DOI: 10.1021/ol3012869
  • Peer Reviewed
• [Journal Article] Kinetic Resolution in Chiral Brønsted Acid Catalyzed Aldol Reaction : Enantioselective Robinson-type Annulation Reaction (2012)
  • Author(s): Yamanaka, M.; Hoshino, M.; Katoh, T.; Mori, K.; Akiyama, T
  • Journal Title: Eur. J. Org. Chem Volume: 2012 Issue: 24 Pages: 4508-4514
  • DOI: 10.1002/ejoc.201200338
  • Peer Reviewed
• [Presentation] Enantioselective Synthesis of Chiral Biaryls by Means of Chiral Phosphoric Acid", Recent Trends in Organocatalysis (2015)
  • Author(s): Takahiko Akiyama
  • Organizer: Pacifichem2015
  • Place of Presentation: Honolulu, Hawaii
  • Year and Date: 2015-12-15
  • Int'l Joint Research / Invited
• [Presentation] Recent Progress in the Chiral Phosphoric Acid Catalysis (2015)
  • Author(s): Takahiko Akiyama
  • Organizer: 21st International Symposium on Fluorine Chemistry
  • Place of Presentation: Como, Italy
  • Year and Date: 2015-08-23
  • Int'l Joint Research / Invited
• [Presentation] Enantioselective Synthesis of Organofluorine Compounds by Means of Chiral Phosphoric Acid (2015)
  • Author(s): Takahiko Akiyama
  • Organizer: IUPAC 2015, 45th World Chemistry Congress
  • Place of Presentation: Busan, Korea
  • Year and Date: 2015-08-09
  • Int'l Joint Research / Invited
• [Presentation] Transfer Hydrogenation Reactions of Ketimines by Means of Chiral Phosphoric Acid (2015)
  • Author(s): Takahiko Akiyama
  • Organizer: The 39th Naito Conference on the Chemistry of Organocatalysts
  • Place of Presentation: Sapporo
  • Year and Date: 2015-07-06
  • Int'l Joint Research / Invited
• [Presentation] Recent Progress in the Chiral Phosphoric Acid Catalysis (2015)
  • Author(s): Takahiko Akiyama
  • Organizer: XIV ICSN Smposium
  • Place of Presentation: Gif-sur-Yvette, France
  • Year and Date: 2015-06-17
  • Int'l Joint Research / Invited
• [Presentation] Enantioselective Synthesis of Organofluorine Compounds by Means of Chiral Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Japan/Russian Conference on Fluorine Chemistry and Friends
  • Place of Presentation: 名古屋工業大学
  • Year and Date: 2014-12-09
  • Int'l Joint Research / Invited
• [Presentation] Friedel-Crafts Alkylation of Indoles by Means of Chiral Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Advanced Molecular Transformations by Organocatalysis, 2nd International Conference & 7th Symposium on Organocatalysis
  • Place of Presentation: 東京大学
  • Year and Date: 2014-11-21
  • Int'l Joint Research / Invited
• [Presentation] Oxidative Kinetic Resolution of Indolines Based on the Enantioselective Transfer Hydrogenation of Ketimines by Means of Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Vietnam Malaysian International Chemical Congress (VMICC))
  • Place of Presentation: Hanoi, Vietnam
  • Year and Date: 2014-11-09
  • Int'l Joint Research / Invited
• [Presentation] Enantioselective Synthesis of Chiral Biaryl Skeleton base on the Bromination of Cs-Symmetric Biaryls by Means of Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: 18th Malaysian International Chemical Congress (18MICC)
  • Place of Presentation: Kala Lumpur, Malaysia
  • Year and Date: 2014-11-05
  • Int'l Joint Research / Invited
• [Presentation] Chiral Phosphoric Acid Catalyzed Enantioselective Reactions (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Chiral China 2014
  • Place of Presentation: Hefei, China
  • Year and Date: 2014-09-29
  • Int'l Joint Research / Invited
• [Presentation] Oxidative Kinetic Resolution of Indolines Based on the Enantioselective Transfer Hydrogenation of Ketimines by Means of Chiral Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: 5th EuCheMS Chemistry Congress
  • Place of Presentation: Istanbul, Turkey
  • Year and Date: 2014-08-31
  • Int'l Joint Research
• [Presentation] Enantioselective Synthesis of Fluorinated Compoudns by Means of Chiral Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Bordeaux Fluorine Days
  • Place of Presentation: Bordeaux, France
  • Year and Date: 2014-07-06
  • Int'l Joint Research / Invited
• [Presentation] Recent Progress in the Chiral Phosphoric Acid Catalysis (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: 20th International Conference on Phosphorus Chemistry
  • Place of Presentation: Dublin, Ireland
  • Year and Date: 2014-06-28
  • Int'l Joint Research / Invited
• [Presentation] Development of Enantioselective Reactions Catalyzed by Chiral Phosphoric Acid (2014)
  • Author(s): Takahiko Akiyama
  • Organizer: Indo-Japanese Conference on Process Chemistry R&D
  • Place of Presentation: Hotel Ramada Plaza Palm Grove, Juhu Mumbai, India
  • Year and Date: 2014-01-30 – 2014-01-31
  • Invited
• [Presentation] Oxidative Kinetic Resolution of Indolines based on Transfer Hydrogenation to Ketimines by means of Chiral Phosphoric Acid (2013)
  • Author(s): Takahiko Akiyama
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2013 (C&FC 2013)
  • Place of Presentation: Renmin University of China, Beijing
  • Year and Date: 2013-12-01 – 2013-12-05
  • Invited
• [Presentation] Oxidative Kinetic Resolution of Indolines base on Transfer Hydrogenation of Ketimines by means of Chiral Phoshoric Acid (2013)
  • Author(s): Takahiko Akiyama
  • Organizer: The 11th International Symposium on Organic Reactions
  • Place of Presentation: Taipei, Taiwan
  • Year and Date: 2013-11-19 – 2013-11-22
  • Invited
• [Presentation] キラルブレンステッド酸触媒反応の新展開 (2013)
  • Author(s): 秋山隆彦
  • Organizer: 第30回有機合成セミナー
  • Place of Presentation: 瀬戸内児島ホテル，倉敷
  • Year and Date: 2013-09-02 – 2013-09-03
  • Invited
• [Presentation] Enantioselective Transfer Hydrogenation of CF3-substituted Ketimines by Means of Chiral Phosphoric Acid (2013)
  • Author(s): Takahiko Akiyama
  • Organizer: 17th European Symposium on Fluorine Chemistry
  • Place of Presentation: Paris, France
  • Year and Date: 2013-07-21 – 2013-07-25
• [Presentation] キラルブレンステッド酸触媒反応の新展開 (2013)
  • Author(s): 秋山隆彦
  • Organizer: 有機合成化学協会関東支部 ミニシンポジウムつくば2013
  • Place of Presentation: 筑波大学，つくば
  • Year and Date: 2013-06-29
  • Invited
• [Presentation] 含フッ素化合物の不斉合成：キラルリン酸触媒を用いるアプローチ (2013)
  • Author(s): 秋山隆彦
  • Organizer: 第10回フッ素相模セミナー
  • Place of Presentation: 東ソー（株）東京研究所，綾瀬
  • Year and Date: 2013-06-06 – 2013-06-07
  • Invited
• [Presentation] Enantioselective Transfer Hydrogenation of Ketimines by Use of Benzothiazoline as a Hydrogen Donor (2013)
  • Author(s): Takahiko Akiyama
  • Organizer: 文部科学省科学研究費補助金「新学術領域研究（研究領域提案型）」「有機分子触媒による未来型分子変換」第1回国際会議（兼）第6回有機触媒シンポジウム
  • Place of Presentation: 大津プリンスホテル，大津
  • Year and Date: 2013-05-18 – 2013-05-19
  • Invited
• [Presentation] Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation of Trifluorimethylated Ketimines (2013)
  • Author(s): Takahiko Akiyama
  • Organizer: 21st Winter Fluorine Conference
  • Place of Presentation: St. Pete Beach, Florida, USA
  • Year and Date: 2013-01-15
  • Invited
• [Presentation] Enantioselective Transfer Hydrogenation by Use of Benzothiazoline (2012)
  • Author(s): Takahiko Akiyama
  • Organizer: Japan-US Organocatalytic Symposium in Hawaii (2012)
  • Place of Presentation: Honolulu, Hawaii
  • Year and Date: 2012-12-16
  • Invited
• [Presentation] Enantioselective Transfer Hydrogenation of Ketimines by Use of Benzothiazoline as a Novel Hydrogen Donor (2012)
  • Author(s): Takahiko Akiyama
  • Organizer: Cambodian Malaysian Chemical Conference (CMCC) 2012
  • Place of Presentation: Siem Reap, Cambodia
  • Year and Date: 2012-10-19
  • Invited
• [Presentation] Enantioselective Synthesis of Organofluorine Compounds by Means of Chiral Br#248;nsted Acid Catalyt (2012)
  • Author(s): Takahiko Akiyama
  • Organizer: Valencia Fluorine Days
  • Place of Presentation: Valencia, Spain
  • Year and Date: 2012-05-21
  • Invited
• [Presentation] キラルリン酸触媒を用いた不斉合成反応の新展開 (2012)
  • Author(s): 秋山隆彦
  • Organizer: 有機合成化学協会九州山口支部平成24年度有機合成化学講演会
  • Place of Presentation: 北九州
  • Invited
• [Presentation] Enantioselective Synthesis of Organofluorine Compounds by Means of Chiral Brønsted Acid Catalyt (2012)
  • Author(s): Takahiko Akiyama
  • Organizer: Valencia Fluorine Days
  • Place of Presentation: Valencia, Spain
  • Invited
• [Presentation] Chiral Phosphoric Acid Catalyzed C(sp3)-H Bond Activation (2011)
  • Author(s): Takahiko Akiyama
  • Organizer: First German-Japan Organocatalytic Symposium
  • Place of Presentation: 京都
  • Invited
• [Presentation] Recent Progress in the Chiral Phosphoric Acid Catalyzed Reactions (2011)
  • Author(s): Takahiko Akiyama
  • Organizer: 10th International Symposium on Organic Reactions (ISOR 10)
  • Place of Presentation: 横浜
  • Invited
• [Presentation] Enantioselective Transfer Hydrogenation of Ketimines by Means of Benzothiazoline as Novel Hydrogen Donor (2011)
  • Author(s): Takahiko Akiyama
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2011 (C&FC2011)
  • Place of Presentation: 奈良
• [Book] Bronsted Acids: Chiral Phosphoric Acid Catalys in Asymmetric Synthesis, in Volume 2, Comprehensive Enantioselecitve Organocatalysis (2013)
  • Author(s): Mori, K.; Akiyama, T.
  • Publisher: Wiley-VCH
• [Book] Georg Thime Verlag KG (2012)
  • Author(s): Takahiko Akiyama
  • Publisher: Section 2.1.1. Asymmetric Organocatalysis, Science of Synthesis, Edited by Keiji Maruoka,
• [Book] Wiley-VCH (2012)
  • Author(s): Takahiko Akiyama
  • Publisher: Synthesis without Metals, in "Handbook of Green Chemistry
• [Book] Wiley-VCH (2012)
  • Author(s): Takahiko Akiyama
  • Publisher: C-C Bond Formation Using Chiral Phoshoric Acid, in Asymetric Synthesis II
• [Book] Elsevier (2012)
  • Author(s): Takahiko Akiyama
  • Publisher: C-C Bond Formation : Mannich Reaction, in Volume 6: Synthetic Methods V -Organocatalysis, Comprehensive Chirality
• [Remarks] 学習院大学理学部化学科 秋山研究室
  • URL: http://www.chem.gakushuin.ac.jp/akiyama/
• [Remarks] 秋山研究室ホームページ
  • URL: http://www.chem.gakushuin.ac.jp/akiyama/
• [Remarks] 学習院大学理学部化学科秋山研究室
  • URL: http://www-cc.gakushuin.ac.jp/~940020/akiyama_site/
• [Remarks] 学習院大学理学部化学科秋山研究室
  • URL: http://www-cc.gakushuin.ac.jp/~940020/akiyama_site/