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A Challenge for Developing Anti-Markovnikov Hydration of Terminal Alkenes

Research Project

Project/Area Number 22655025
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

KONDO Teruyuki  京都大学, 学際融合教育研究推進センター・先端医工学研究ユニット, 教授 (20211914)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,520,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥1,700,000 (Direct Cost: ¥1,700,000)
Keywordsパラジウム / ルテニウム / アルケン / イソプレノール / 反マルコフニコフ則 / アルコール / 酸化反応 / 環化反応 / 反マルコフニコフ / テトラヒドロフラン
Research Abstract

We have examined the cyclization of isoprenol in the presence of several transition-metal catalysts, and found that the cyclization of isoprenol occurred smoothly in alcohols under 1 atm of O2 by using a catalyst system of PdCl_2 and CuCl_2, to give 2-alkoxy-3-methyltetrahydrofuran, not to oxetane. This result clearly indicated that the present catalyst system realized anti-Markovnikov-type intramolecular addition of hydroxyl group to a terminal C=C bond in isoprenol. As a result, the present study offered the fundamental and important methodology, which are essential for developing transition-metal catalyzed anti-Markovnikov hydration of terminal alkenes.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (41 results)

All 2012 2011 2010 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (26 results) Book (4 results) Remarks (3 results)

  • [Journal Article] New Catalytic Performances of Ruthenium and Rhodium Complexes Directed toward Organic Synthesis with High Atom Efficiency2011

    • Author(s)
      Teruyuki Kondo
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: Vol.84, No.5 Pages: 441-458

    • NAID

      10028241085

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Simple and Practical Aerobic Oxidation of Alcohols Catalyzed by a (μ-Oxo) tetraruthenium Cluster2011

    • Author(s)
      Teruyuki Kondo
    • Journal Title

      Green and Sustainable Chemistry

      Volume: 1 Pages: 149-154

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Substrate/Product-targeted NMR monitoring of pyrimidine catabolism and its inhibition by a clinical drug.2011

    • Author(s)
      Yamada H, Mizusawa K, Igarashi R, Tochio H, Shirakawa M, Tabata Y, Kimura Y, Kondo T, Aoyama Y, Sando S.
    • Journal Title

      ACS Chem Biol.

      Volume: 7 Issue: 3 Pages: 535-542

    • DOI

      10.1021/cb2003972

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple and Practical Aerobic Oxidation of Alcohols Catalyzed by a(μ-Oxo) tetra-ruthenium Cluster2010

    • Author(s)
      Teruyuki Kondo, Yu Kimura, TakashiKanda, Daisuke Takagi, Kenji Wada, Akio Toshimitsu
    • Journal Title

      Green and Sustainable Chemistry

      Volume: Vol.1, No.4 Pages: 149-154

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Yasushi Shiraki Selective Trimerization of Ethylene to Isohexenes Catalyzed by Ruthenium(0) Complex2010

    • Author(s)
      Teruyuki Kondo, Keisuke Yamamoto, Daisuke Takagi, Lingfeng Shen, Yuki Yoshida, Yu Kimura, Akio Toshimitsu, Masahiko Kuramoto
    • Journal Title

      Chem Cat Chem

      Volume: Vol.2, No.12 Pages: 1565-1568

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes2010

    • Author(s)
      Teruyuki Kondo, Masatsugu Niimi, Yuki Yoshida, Kenji Wada, Take-aki Mitsudo, Yu Kimura and Akio Toshimitsu
    • Journal Title

      Molecules

      Volume: Vol.15, No.6 Pages: 4189-4200

    • NAID

      120003477806

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Selective Trimerization of Ethylene to Isohexenes Catalyzed by Ruthenium(0) Complex2010

    • Author(s)
      Teruyuki Kondo
    • Journal Title

      ChenCatChem

      Volume: 2(12) Pages: 1565-1568

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-catalyzed Linear Codimerization and Cycloaddition of Ketenes with Alkynes2010

    • Author(s)
      Teruyuki Kondo
    • Journal Title

      Molecules

      Volume: 15(6) Pages: 4189-4200

    • NAID

      120003477806

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] ルテニウム錯体触媒を用いるジエンとアルケンとの鎖状共二量化反応2012

    • Author(s)
      近藤輝幸, 他
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] ルテニウム錯体触媒を用いるシクロプロペノン類とアルケンとの脱カルボニル化カップリング反応2012

    • Author(s)
      近藤輝幸, 他
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] Synthesis and Functional Evaluation of a Dendrimer-amine Coordinated Gd-MRI contrast Agent2012

    • Author(s)
      Teruyuki Kondo
    • Organizer
      The 3rd Taiwan-Japan Symposium on Nanomedicine
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-03-08
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis and Functional Evaluation of a Dendrite-amine Coordinated Gd-MRI contrast Agent2012

    • Author(s)
      Teruyuki Kondo
    • Organizer
      The 3rd Taiwan-Japan Symposium on Nanomedicine
    • Place of Presentation
      京都(Invited Lecture)
    • Year and Date
      2012-03-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Ruthenium-Catalyzed Oligomerization and Co-oligomerization of Alkenes with High Atom-Efficiency2012

    • Author(s)
      Teruyuki Kondo
    • Organizer
      The 6th Pure and Applied Chemistry International Conference 2011(PACCON2012)
    • Place of Presentation
      Chiang Mai, Thailand
    • Year and Date
      2012-01-12
    • Related Report
      2011 Final Research Report
  • [Presentation] Ruthenium-Catalyzed Oligomerization and Co-oligomerization of Alkenes with High Atom-Efficiency2012

    • Author(s)
      Teruyuki Kondo
    • Organizer
      The 6th Pure and Applied Chemistry International Conference 2011 (PACCON 2012)
    • Place of Presentation
      Chiang Mai, Thailand(Invited Lecture)
    • Year and Date
      2012-01-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] Ruthenium-Catalyzed Oligomerization and Co-oligomerization of Alkenes with High Atom-Efficiency2011

    • Author(s)
      Teruyuki Kondo
    • Organizer
      14th Asian Chemical Congress 2011(14 ACC)
    • Place of Presentation
      Bangkok, Thailand
    • Year and Date
      2011-09-06
    • Related Report
      2011 Final Research Report
  • [Presentation] Ruthenium-Catalyzed Oligomerization and Co-ollgomerization of Alkenes with High Atom-Efficiency2011

    • Author(s)
      Teruyuki Kondo
    • Organizer
      14th Asian Chemical Congress 2011 (14 ACC)
    • Place of Presentation
      Bangkok, Thailand(Invited Lecture)
    • Year and Date
      2011-09-06
    • Related Report
      2011 Annual Research Report
  • [Presentation] ヘテロメタラサイクルを鍵中間体とする新規触媒的ヘテロ環構築法有機合成化学研究所2011

    • Author(s)
      近藤輝幸
    • Organizer
      平成23年度第1回産学共同学習セミナー「新物質・新材料研究会」
    • Place of Presentation
      京都
    • Year and Date
      2011-07-21
    • Related Report
      2011 Final Research Report
  • [Presentation] ヘテロメタラサイクルを鍵中間体とする新規触媒的ヘテロ環構築法2011

    • Author(s)
      近藤輝幸
    • Organizer
      有機合成化学研究所平成23年度第1回産学共同学習セミナー「新物質・新材料研究会」
    • Place of Presentation
      京都(招待講演)
    • Year and Date
      2011-07-21
    • Related Report
      2011 Annual Research Report
  • [Presentation] ルテニウム錯体触媒を用いる分子間Pauson-Khand型反応の選択性制御2011

    • Author(s)
      近藤輝幸, 他
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] カルボジイミド、アルキンおよび一酸化炭素の新規触媒的分子間[2+ 2+ 1]共付加環化反応2011

    • Author(s)
      近藤輝幸, 他
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] カルボジイミド、アルキンおよび一酸化炭素の新規触媒的分子間[2+2+1]共付加環化反応2011

    • Author(s)
      近藤輝幸
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜市)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] ルテニウム錯体触媒を用いる分子間Pauson-Khand型反応の選択性制御2011

    • Author(s)
      近藤輝幸
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜市)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Catalytic activity of a novel(μ-oxo) tetrar-utheniumcluster towards selective oxidation of alcohols and dehydrogenative cylclization of 2-aminophenetyl alcohols2010

    • Author(s)
      Teruyuki Kondo, 他
    • Organizer
      The International Chemical Congress of Pacific Basin Societies(Pacifichem 2010)
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2011 Final Research Report
  • [Presentation] Catalytic activity of a novel (μ-oxo)tetraruthenium cluster towards selective oxidation of alcohols and dehydrogenative cylclization of 2-aminophenetyl alcohols2010

    • Author(s)
      Teruyuki Kondo
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Hawaii Convention Center (Honolulu, U.S.A)
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] ロジウム触媒を用いたケテン・イソチオシアナートによるロダニン誘導体合成反応2010

    • Author(s)
      近藤輝幸
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-16
    • Related Report
      2011 Final Research Report
  • [Presentation] ロジウム触媒を用いたケテン・イソチオシアナートによるロダニン誘導体合成反応2010

    • Author(s)
      近藤輝幸
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台市民会館(仙台市)
    • Year and Date
      2010-10-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] 高感度MRI造影剤としてのキラルデドリマーアミン配位Gd錯体の合成と機能評価2010

    • Author(s)
      近藤輝幸
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2010-09-27
    • Related Report
      2011 Final Research Report
  • [Presentation] 高感度MRI造影剤としてのキラルデンドリマーアミン配位Gd錯体の合成と機能評価2010

    • Author(s)
      近藤輝幸
    • Organizer
      第60回錯体化学討論会
    • Place of Presentation
      大阪国際交流センター(大阪市)(招待講演)
    • Year and Date
      2010-09-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 高感度MRI造影剤としてのキラルデンドリマーアミン配位Gd錯体の合成と機能評価2010

    • Author(s)
      近藤輝幸, 他
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      八王子市
    • Year and Date
      2010-09-18
    • Related Report
      2011 Final Research Report
  • [Presentation] 高感度MRI造影剤としてのキラルデンドリマーアミン配位Gd錯体の合成と機能評価2010

    • Author(s)
      近藤輝幸
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学(八王子市)
    • Year and Date
      2010-09-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Rhodium-catalyzed Synthesis of Rhoda-nines from Ketenes and Isothiocyanates2010

    • Author(s)
      Teruyuki Kondo, et al
    • Organizer
      24th International Conference on Organo-metallic Chemistry(ICOMC2010)
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      2010-07-19
    • Related Report
      2011 Final Research Report
  • [Presentation] Rhodium-catalyzed Synthesis of Rhodanines from Ketenes and Isothiocyanates2010

    • Author(s)
      Teruyuki Kondo
    • Organizer
      24th International Conference on Organometallic Chemistry (ICOMC2010)
    • Place of Presentation
      Taipei International Convention Center (Taipei, Taiwan)
    • Year and Date
      2010-07-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Ruthenium-catalyzed Selective Co-oligomerization of Different Alkenes with High Atom-Efficiency2010

    • Author(s)
      Teruyuki Kondo
    • Organizer
      BIT's 1st Annual World Congress of Catalytic Asymmetric Synthesis 2010
    • Place of Presentation
      Beijing, China
    • Year and Date
      2010-05-21
    • Related Report
      2011 Final Research Report
  • [Presentation] Ruthenium-catalyzed Selective Co-oligomerization of Different Alkenes with High Atom-Efficiency2010

    • Author(s)
      Teruyuki Kondo
    • Organizer
      BTT's 1^<st> Annual World Congress of Catalytic Asymmetric Synthesis 2010
    • Place of Presentation
      Beijing International Convention Center (Beijing, China)(招待講演)
    • Year and Date
      2010-05-21
    • Related Report
      2010 Annual Research Report
  • [Book] 日本発ブロックバスターを目指して-創薬研究の最前線-2010

    • Author(s)
      近藤輝幸
    • Publisher
      シーエムシー出版
    • Related Report
      2011 Final Research Report
  • [Book] 使える!有機合成反応241実践ガイド2010

    • Author(s)
      近藤輝幸
    • Publisher
      化学同人
    • Related Report
      2011 Final Research Report
  • [Book] 日本発ブロックバスターを目指して-創薬研究の最前線-2010

    • Author(s)
      近藤輝幸
    • Publisher
      (株)シーエムシー出版
    • Related Report
      2010 Annual Research Report
  • [Book] 使える!有機合成反応241実践ガイド2010

    • Author(s)
      近藤輝幸
    • Publisher
      (株)化学同人
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.probe.abe.kyoto-u.ac.jp/index.html

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.probe.abe.kyoto-u.ac.jp/index.html

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.probe.abe.kyoto-u.ac.jp/index.html

    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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