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Synthesis of Chiral Amino Acids by Using CO2 as a C1 Source

Research Project

Project/Area Number 26293001
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionHokkaido University

Principal Investigator

SATO Yoshihiro  北海道大学, 薬学研究院, 教授 (90226019)

Research Collaborator SAITO Nozomi  
OONISHI Yoshihiro  
MITA Tsuyoshi  
DOI Ryohei  
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Fiscal Year 2017: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2016: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2015: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2014: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Keywordsカルボキシル化反応 / αーアミノ酸 / βーアミノ酸 / 不斉合成 / ニッケル / コバルト / 二酸化炭素 / カルボン酸 / カルボキシル化 / パラジウム / ロジウム / 二酸化炭素固定 / アミノ酸 / 触媒的不斉合成 / 環境調和 / 炭素固定 / 環境調和型反応 / α-アミノ酸 / β-アミノ酸
Outline of Final Research Achievements

Carbon dioxide (CO2) is attractive to synthetic organic chemists as an abundant, cheap, and non-toxic carbon source. Although CO2 is very stable chemical substances, it has mainly two reactivities; one is electrophilicity of the center carbon of CO2, and the other is that C=O double bond can be activated by transition metal complexes. With respect to the former reactivity, we developed the synthesis of chiral a-amino acids through Cu-catalyzed asymmetric addition of silyl anion to N-sulfonyl imine followed by the reaction of the resultant chiral a-silyl N-sulfoneamide with CO2 in a stereoretentive manner. With respect to the latter reactivity, we developed the synthesis of a chiral b-amino acids or b-aryloxy carboxylic acids through a combination of nickel-catalyzed carboxylation of ynamides or aryl ynol ethers and rhodium-catalyzed asymmetric hydrogenation of the resultant carboxylated product.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (46 results)

All 2018 2017 2016 2015 2014 Other

All Journal Article (23 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 23 results,  Acknowledgement Compliant: 14 results,  Open Access: 3 results) Presentation (19 results) (of which Int'l Joint Research: 9 results,  Invited: 5 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO22017

    • Author(s)
      Kenichi Michigami, Tsuyoshi Mita, Yoshihiro Sato
    • Journal Title

      Journal of the American Chemical Society

      Volume: 139 Issue: 17 Pages: 6094-6097

    • DOI

      10.1021/jacs.7b02775

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Intramolecular Arylative Carboxylation of Allenes with CO2 for the Construction of 3-Substituted Indole-2-carboxylic Acids2017

    • Author(s)
      Higuchi, Y.; Mita, T.; Sato, Y.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 10 Pages: 2710-2713

    • DOI

      10.1021/acs.orglett.7b01055

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel-Catalyzed Hydrocarboxylation of Ynamides with CO2 and H2O: An Observation of Unexpected Regioselectivity2017

    • Author(s)
      Ryohei Doi, Iman Abdullah, Takahisa Taniguchi, Nozomi Saito, Yoshihiro Sato
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 55 Pages: 7720-7723

    • DOI

      10.1039/c7cc03127k

    • NAID

      120006488397

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ligand-free Suzuki?Miyaura coupling using ruthenium(0) nanoparticles and a continuously irradiating microwave system2017

    • Author(s)
      Akiyama Toshiki、Taniguchi Takahisa、Saito Nozomi、Doi Ryohei、Honma Tetsuo、Tamenori Yusuke、Ohki Yuuta、Takahashi Naoyuki、Fujioka Hiromichi、Sato Yoshihiro、Arisawa Mitsuhiro
    • Journal Title

      Green Chemistry

      Volume: 19 Issue: 14 Pages: 3357-3369

    • DOI

      10.1039/c7gc01166k

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Co-Catalyzed Direct Addition of Allylic C(sp3-H Bonds to Ketones2017

    • Author(s)
      Mita, T.: Hanagata, S.; Michikami, K.; Sato, Y.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 21 Pages: 5876-5879

    • DOI

      10.1021/acs.orglett.7b02871

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoretentive Addition of N-tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines2016

    • Author(s)
      Tsuyoshi Mita, Keisuke Saito, Masumi Sugawara, Yoshihiro Sato
    • Journal Title

      Chemistry An Asian Journal

      Volume: 11 Issue: 10 Pages: 1528-1531

    • DOI

      10.1002/asia.201600270

    • Related Report
      2016 Annual Research Report 2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Carboxylation of Activated Vinylcyclopropanes with CO22016

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, and Yoshihiro Sato
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 11 Pages: 2754-2757

    • DOI

      10.1021/acs.orglett.6b01231

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-Pot Synthesis of α-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration2016

    • Author(s)
      Tsuyoshi Mita, Masumi Sugawara, Yoshihiro Sato
    • Journal Title

      Journal of Organic Chemistry

      Volume: 81 Issue: 12 Pages: 5236-5243

    • DOI

      10.1021/acs.joc.6b00837

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Self-Assembled Multilayer-Stabilized Nickel Nanoparticle Catalyst for Ligand-Free Cross-Coupling Reactions: in situ Metal Nanoparticle and Nanospace Simultaneous Organization2016

    • Author(s)
      Naoyuki Hoshiya, Katsumasa Fujiki, Takahisa Taniguchi, Tetsuo Honma, Yusuke Tamenori, Mincen Xiao, Nozomi Saito, Mami Yokoyama, Akira Ishii, Hiromichi Fujioka, Satoshi Shuto, Yoshihiro Sato, Mitsuhiro Arisawa
    • Journal Title

      Adv. Synth. Catal.

      Volume: 358 Pages: 2449-2459

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium(I)-Catalyzed Diastereoselective Cycloisomerization of Enynes with Tethered (S)-2-Methyl-2-propanesulfinyl Imine2016

    • Author(s)
      Yoshihiro Oonishi, Yoshio Hato, Yoshihiro Sato
    • Journal Title

      Adv. Synth. Catal.

      Volume: 358 Issue: 14 Pages: 2273-2279

    • DOI

      10.1002/adsc.201600310

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereoselective Construction of Spiro-Fused Tricyclic Frameworks by Sequential Reaction of Enynes, Imines, and Diazoalkenes with Rh(I) and Rh(II) Catalysts2016

    • Author(s)
      Yoshio Hato, Yoshihiro Oonishi, Yasunori Yamamoto, Kiyohiko Nakajima, Yoshihiro Sato
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 17 Pages: 7847-7854

    • DOI

      10.1021/acs.joc.6b01502

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Enantioselective Synthesis of β-Amino Acid Derivatives via Nickel-Promoted Regioselective Carboxylation of Ynamides and Rhodium-Catalyzed Asymmetric Hydrogenation2016

    • Author(s)
      Nozomi Saito, Iman Abdullah, Kayoko Hayashi, Katsuyuki Hamada, Momoko Koyama, Yoshihiro Sato
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 42 Pages: 10080-10089

    • DOI

      10.1039/c6ob01234e

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization2015

    • Author(s)
      Yoshihiro Oonishi, Akira Saito, Yoshihiro Sato
    • Journal Title

      Asian J. Org. Chem.

      Volume: 4 Issue: 1 Pages: 81-86

    • DOI

      10.1002/ajoc.201402239

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Nickel-Promoted Highly Regioselective Carboxylation of Aryl Ynol Ether and Its Application to the Synthesis of Chiral β-Aryloxypropionic Acid Derivatives2015

    • Author(s)
      齋藤 望、孫 仲冬、佐藤美洋
    • Journal Title

      Chemistry an Asian Journal

      Volume: 10 Issue: 5 Pages: 1170-1176

    • DOI

      10.1002/asia.201403399

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Double Carbonylation of Aryl Iodides with Amines under an Atmospheric Pressure of Carbon Monoxide Using Sulfur- Modified Au-Supported Palladium2015

    • Author(s)
      Nozomi Saito Takahisa Taniguchi, Naoyuki Hoshiya, Satoshi Shuto, Mitsuhiro Arisawa, Yoshihiro Sato
    • Journal Title

      Green Chem.

      Volume: 17 Issue: 4 Pages: 2358-2361

    • DOI

      10.1039/c4gc02469a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO22015

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, Yoshihiro Sato
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 46 Pages: 16391-16394

    • DOI

      10.1002/chem.201503359

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions2015

    • Author(s)
      Tsuyoshi Mita, Kenta Suga, Kaori Sato, Yoshihiro Sato
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 21 Pages: 5276-5279

    • DOI

      10.1021/acs.orglett.5b02645

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium(I)-Catalyzed [2+2+2] Cycloaddition between Allene, Alkyne, and Imine via a Strained Azarhodacycle Intermediate2015

    • Author(s)
      Yoshihiro Oonishi, Yoshio Hato, Yoshihiro Sato
    • Journal Title

      Adv. Syn. Catal.

      Volume: 357 Issue: 14-15 Pages: 3033-3039

    • DOI

      10.1002/adsc.201500417

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Carboxylation with CO_2 via Brook Rearrangement : Preparation of α-Hydroxy Acid Derivatives2014

    • Author(s)
      Tsuyoshi Mita, Yuki Higuchi, and Yoshihiro Sato
    • Journal Title

      Org. Lett

      Volume: 16 Issue: 1 Pages: 14-17

    • DOI

      10.1021/ol403099f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nickel(0)-Promoted Carboxylation of Allenamides with Carbon Dioxide via a Nickelalactone Intermediate2014

    • Author(s)
      Nozomi Saito, Yasuyuki Sugimura, Yoshihiro Sato
    • Journal Title

      Synlett

      Volume: 25 Issue: 05 Pages: 736-740

    • DOI

      10.1055/s-0033-1340628

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Arylglycines from CO_2 through α-Amino Organomanganese Species2014

    • Author(s)
      Tsuyoshi Mita, Jianyang Chen, and Yoshihiro Sato
    • Journal Title

      Org. Lett

      Volume: 16 Issue: 8 Pages: 2200-2203

    • DOI

      10.1021/ol500701n

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ru-Catalyzed C-H Silylation of 1-Arylpyrazole Derivatives and Fluoride-Mediated Carboxylation: Use of Two Nitrogen Atomes of the Pyrazole Group2014

    • Author(s)
      Tsuyoshi Mita, Hiroyuki Tanaka, Kenichi Michigami, Yoshihiro Sato
    • Journal Title

      Synlett

      Volume: 25 Issue: 09 Pages: 1291-1294

    • DOI

      10.1055/s-0033-1341230

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Catalytic Enantioselective Silylation of N-Sulfonylimines: Asymmetric Synthesis of α-Amino Acids from CO2 via Stereospecific Carboxylation of α-Amino Silanes2014

    • Author(s)
      Tsuyoshi Mita, Masumi Sugawara, Keisuke Saito, and Yoshihiro Sato
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 11 Pages: 3028-3031

    • DOI

      10.1021/ol501143c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] CO2を一炭素源として用いた新規触媒的ダブルカルボキシル化反応の開発2018

    • Author(s)
      石井聖、樋口裕紀、美多剛、佐藤美洋
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 二酸化炭素を用いるアリル位C(sp3)-H結合の触媒的カルボキシル化反応2017

    • Author(s)
      美多剛、道上健一、佐藤美洋
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of b-aryloxy carboxylic acid and b-amino acid derivatives via regioselective carboxylation of polarized alkynes with CO22016

    • Author(s)
      Yoshihiro Sato
    • Organizer
      Catalysis and Fine Chemicals (C&FC) 2016
    • Place of Presentation
      Taipei (台湾)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cobalt-Catalyzed Carboxylation of Allylic C-H Bond with Carbon Dioxide2016

    • Author(s)
      Kenichi Michigami, Tsuyoshi Mita, Yoshihiro Sato
    • Organizer
      The 11th International Conference on Cutting-Edge Organic Chemistryin Asia
    • Place of Presentation
      Daejeon(韓国)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of a-amino acids through CO2 incorporation2016

    • Author(s)
      Yoshihiro Sato
    • Organizer
      The 11th International Conference on Cutting-Edge Organic Chemistryin Asia
    • Place of Presentation
      Daejeon(韓国)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 硫黄修飾金担持型ニッケル触媒SANi の開発と二酸化炭素固定化反応への利用2016

    • Author(s)
      谷口 敬寿、齋藤 望、星谷 尚亨、藤木 勝将、周東 智、藤岡 弘道、有澤 光弘、佐藤 美洋
    • Organizer
      第14回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京都渋谷区)
    • Year and Date
      2016-05-27
    • Related Report
      2016 Annual Research Report
  • [Presentation] Copper-Catalyzed Enantioselective Silylation Followed by Stereoretentive Addition to Carbon Electrophiles2016

    • Author(s)
      Tsuyoshi Mita, Masumi Sugawara, Keisuke Saito, Yoshihiro Sato
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      ナレッジキャピタル コングレコンベンションセンター(大阪府大阪市)
    • Year and Date
      2016-04-20
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] アンモニウムイリドのカルボキシル化を経由する CO2を用いたα-アミノ酸のワンポット合成2015

    • Author(s)
      菅原真純、美多剛、佐藤美洋
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      早稲田大学(東京都新宿区)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] Nickel-Mediated and -Catalyzed Carboxylation of Ynamide and Its Application to the Enantioselective Synthesis of b-Amino Acis Derivatives2015

    • Author(s)
      Iman Abdullah, Nozomi Saito, Kayoko Hayashi, Katsuyuki Hamada, Momoko Koyama, Yoshihiro Sato
    • Organizer
      IKCOC13
    • Place of Presentation
      リーガロイヤルホテル京都(京都府京都市)
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Rh(I)-Catalyzed Asymmetric Cyclization of Enynes via C(sp3)-H Bond Activation2015

    • Author(s)
      Shunki Sakamoto, Yoshihiro Oonishi, Yoshihiro Sato
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府吹田市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] Nickel-Catalyzed Carboxylation of Alkynes Using Sulfur-Modified Au-Supported Nickel Nanoparticles Catalyst (SANi)2015

    • Author(s)
      Takahisa Taniguchi, Nozomi Saito, Naoyuki Hoshiya, Katsumasa Fujiki, Satoshi Shuto, Tetsuo Honma, Hiromichi Fujioka, Mitsuhiro Arisawa, Yoshihiro Sato
    • Organizer
      OMCOS18
    • Place of Presentation
      シッチェス(スペイン)
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Nickel-Promoted Carboxylation of Alkenes: Synthesis of Acrylic Acid Derivatives2015

    • Author(s)
      Naoya Awaji, Naoto Taguchi, Nozomi Saito, Takahisa Taniguchi, Yoshihiro Sato
    • Organizer
      OMCOS18
    • Place of Presentation
      シッチェス(スペイン)
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Carboxylation of Halocarbons with CO2 Using a Structurally Strained Disilane2015

    • Author(s)
      Kenta Suga, Tsuyoshi Mita, Kaori Sato, Yoshihiro Sato
    • Organizer
      OMCOS18
    • Place of Presentation
      シッチェス(スペイン)
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-Pot Synthesis of α-Amino Acids from CO2 and Imine Equivalents2015

    • Author(s)
      Tsuyoshi Mita, Masumi Sugawara, Jianyang Chen, Yuki Higuchi, Yoshihiro Sato
    • Organizer
      Organic Chemistry Symposium, Royal Society of Chemistry Roadshow
    • Place of Presentation
      東北大学青葉サイエンスホール(宮城県仙台市)
    • Year and Date
      2015-06-01
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] イリジウム触媒によるエナンチオ選択的C-Hホウ素化反応の開発2015

    • Author(s)
      美多剛、池田祐人、佐藤美洋
    • Organizer
      日本薬学会135年会
    • Place of Presentation
      デザイン・クリエイティブセンター神戸(神戸)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] ニッケル錯体によるイノールエーテルのカルボキシル化と不斉水素化を経由したβ-アリールオキシカルボン酸類のエナンチオ選択的合成2014

    • Author(s)
      齋藤望、孫仲冬、佐藤美洋
    • Organizer
      第40回反応と合成の進歩シンポジウム、
    • Place of Presentation
      東北大学百周年記念会館(仙台)
    • Year and Date
      2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] Nickel(0)-Promoted Carboxylation of Aryl Ynol Ether with CO22014

    • Author(s)
      孫仲冬、齋藤望、佐藤美洋
    • Organizer
      ICOMC 2014
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] One-Pot Synthesis of a-Amino Acids and a-Hydroxy Acids from Aldehydes and Carbon Dioxide2014

    • Author(s)
      樋口裕紀、美多剛、佐藤美洋
    • Organizer
      ICOMC 2014
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] 芳香族C-H結合の触媒的シリル化、続く二酸化炭素によるカルボキシル化反応の開発2014

    • Author(s)
      田中寛之、道上健一、美多剛、佐藤美洋
    • Organizer
      日本薬学会北海道支部第142回例会
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      2014-05-24
    • Related Report
      2014 Annual Research Report
  • [Book] 二酸化炭素を用いた化学品製造技術(第2章第7節 二酸化炭素を一炭素源として用いるαーアミノ酸の化学合成)2016

    • Author(s)
      美多剛,佐藤美洋(分担執筆)(杉本裕 監修)
    • Total Pages
      306
    • Publisher
      S&T出版
    • Related Report
      2016 Annual Research Report
  • [Book] 二酸化炭素を用いた化学品製造技術2016

    • Author(s)
      美多剛,佐藤美洋(監修 杉本裕)
    • Total Pages
      306
    • Publisher
      S&T出版
    • Related Report
      2015 Annual Research Report
  • [Remarks] 北海道大学大学院薬学研究院精密合成化学研究室ホームページ

    • URL

      http://gouka.pharm.hokudai.ac.jp/FSC/publications/publication.htm

    • Related Report
      2015 Annual Research Report
  • [Remarks] 北海道大学大学院薬学研究院 精密合成科学研究室ホームページ

    • URL

      http://gouka.pharm.hokudai.ac.jp

    • Related Report
      2014 Annual Research Report

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Published: 2014-04-04   Modified: 2019-03-29  

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