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Lithium Amide in Consecutive Aminolithiation-Carbolithiation

Research Project

Project/Area Number 24590035
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionDoshisha Women's College of Liberal Arts

Principal Investigator

Tomioka Kiyoshi  同志社女子大学, 薬学部, 教授 (50114575)

Project Period (FY) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords有機化学 / 薬学 / カルバニオン / 合成化学 / 活性種
Outline of Final Research Achievements

An addition reaction of nitrogen nucleophiles to C=C double bonds is important for C-N bond formation. Addition of lithium amides to olefins affords alkyllithiums, which is powerful nucleophiles and useful for additional bond forming reactions. We developed consecutive aminolithiation-carbolithiation reactions, and asymmetric one-pot [N+2+n] cyclization reactions. Asymmetric total synthesis of some natural products was also achieved by using our developed reactions.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (32 results)

All 2015 2014 2013 2012 2011 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results,  Acknowledgement Compliant: 3 results) Presentation (14 results) (of which Int'l Joint Research: 1 results,  Invited: 14 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Cyclic Model for the Asymmetric Conjugate Addition of Organolithiums with Enoates2015

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Synthesis

      Volume: 47 Issue: 15 Pages: 2256-2264

    • DOI

      10.1055/s-0034-1380702

    • NAID

      120005674638

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Exploration of Dimethylzinc-Mediated Radical Reactions.2015

    • Author(s)
      K. Yamada
    • Journal Title

      Chem. Rec.

      Volume: 15 Issue: 5 Pages: 854-871

    • DOI

      10.1002/tcr.201500017

    • NAID

      120005689178

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Contiguous radical pivaloyloxymethylation-directed C(sp3)-H iodination of N-tosyl cycloalkanecarbaldimine.2015

    • Author(s)
      Kiyoshi Tomioka
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 23 Pages: 3086-3089

    • DOI

      10.1016/j.tetlet.2014.11.105

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Short Synthesis of (+)-β-Lycorane by Asymmetric Conjugate Addition Cascade.2015

    • Author(s)
      Kiyoshi Tomioka
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 39 Pages: 7222-7226

    • DOI

      10.1016/j.tet.2015.03.014

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-pot synthesis of N-heterocycles by a tandem addition reaction of ω-alkenylmagnesium bromide with C=N double bond–oxidative bromolactamization2014

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Issue: 32 Pages: 4313-4315

    • DOI

      10.1016/j.tetlet.2013.06.002

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of 8-epi-Javaberine A and Javaberine A2014

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 2 Pages: 1311-1321

    • DOI

      10.3987/com-13-s(s)101

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Addition and in situ halo-cyclization of ω-alkenyl Grignard reagents with aldehydes, ketones, carbon dioxide, and azodicarboxylate2013

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      New J. Chem.

      Volume: 37 Issue: 12 Pages: 3873-3876

    • DOI

      10.1039/c3nj00765k

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Critical Profiles of Chiral Diether-Mediated Asymmetric Conjugate Aminolithiation of Enoate with Lithium Amide as a Key to the Total Synthesis of (-)-Kopsinine2013

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 15 Pages: 3264-3273

    • DOI

      10.1016/j.tet.2013.02.035

    • NAID

      120005244223

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] NMR studies on the structure of a lithium amide-chiral diether complex for an asymmetric reaction2013

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 19 Pages: 3836-3840

    • DOI

      10.1016/j.tet.2013.03.036

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Kopsinine by the Asymmetric One-Pot [N+2+3] Cyclization2012

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Chem. Asian J.

      Volume: 7 Issue: 10 Pages: 2196-2198

    • DOI

      10.1002/asia.201200575

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis of (S)-Laudanosine by Hydroamination2012

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      Heterocycles

      Volume: 86 Issue: 1 Pages: 469-485

    • DOI

      10.3987/com-12-s(n)44

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] General Entry to Asymmetric One-Pot [N+2+n] Cyclization for the Synthesis of 3- to 7-Membered Azacycloalkanes2012

    • Author(s)
      Yasutomo Yamamoto
    • Journal Title

      J. Org. Chem.

      Volume: 77 Issue: 17 Pages: 7212-7222

    • DOI

      10.1021/jo301495a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-trans-Dihydronarciclasine Utilizing Asymmetric Conjugate Addition.2012

    • Author(s)
      Kiyoshi Tomioka
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 23 Pages: 5868-5871

    • DOI

      10.1021/ol302757y

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Steric Influence of N-Phosphorus-arylimines on the Rhodium-Catalyzed Asymmetric Arylation2011

    • Author(s)
      Hao, X.; Chen, Q.; Yamada, K.; Yamamoto, Y.; Tomioka, K
    • Journal Title

      Tetrahedron

      Volume: 67(35) Issue: 22 Pages: 6469-6473

    • DOI

      10.1016/j.tet.2012.03.107

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Short step asymmetric synthesis of complex molecules2015

    • Author(s)
      富岡清
    • Organizer
      Pacifichem2015
    • Place of Presentation
      ヒルトンハワイアンビレッジ(ホノルル)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 並列直列水素結合の有機化学2015

    • Author(s)
      富岡清
    • Organizer
      岐阜大学特別講演会
    • Place of Presentation
      岐阜大学工学部(岐阜)
    • Year and Date
      2015-05-15
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 医薬プロセス化学の科学と生産技術2015

    • Author(s)
      富岡清
    • Organizer
      CPhI Japan 2015
    • Place of Presentation
      東京ビッグサイト(東京)
    • Year and Date
      2015-04-22
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 力量あるプロセス化学2014

    • Author(s)
      富岡 清
    • Organizer
      日本プロセス化学会 2014ウィンターシンポジウム
    • Place of Presentation
      富山国際会議場(富山)
    • Year and Date
      2014-12-05
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Paradigm re-shift of medicinal chemistry in Japan2014

    • Author(s)
      富岡 清
    • Organizer
      ドイツ薬学会年会
    • Place of Presentation
      ゲーテ大学(フランクフルト)
    • Year and Date
      2014-09-24 – 2014-09-26
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Radicals by Chance2014

    • Author(s)
      富岡 清
    • Organizer
      CBC-Symposium on Free Radical Chemistry
    • Place of Presentation
      ナンヤン工科大学(シンガポール)
    • Year and Date
      2014-04-25
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 彼岸花科アルカロイド類の不斉全合成2013

    • Author(s)
      富岡 清
    • Organizer
      第48回天然物化学談話会
    • Place of Presentation
      アヤハレークサイドホテル(滋賀)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 生産性プラス法則性-医薬プロセス化学の展望2013

    • Author(s)
      富岡 清
    • Organizer
      合同シンポジウム- 日本プロセス化学会 2013 ウインターシンポジウム・新学術領域研究「有機分子触媒による未来型分子変換」第3回公開シンポジウム-
    • Place of Presentation
      仙台市民会館(宮城)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ithium Amide in Consecutive Aminolithiation-Carbolithiation2013

    • Author(s)
      富岡 清
    • Organizer
      14th Tetrahedron Symposium
    • Place of Presentation
      Seoul (Korea)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Lithium amide-Chiral Diether as A Powerful Asymmetric Aminating Reagent2013

    • Author(s)
      富岡 清
    • Organizer
      11st International Symposium of Organic Reactions (ISOR11)
    • Place of Presentation
      Taipei (Taiwan)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] リチウムアミドを駆使する合成化学

    • Author(s)
      富岡 清
    • Organizer
      九州大学先導物質化学研究所講演会
    • Place of Presentation
      九州大学 先導物質化学研究所(福岡)
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 彼岸花科アルカロイドの不斉全合成

    • Author(s)
      富岡清
    • Organizer
      浜理薬品特別講演会
    • Place of Presentation
      浜理薬品(大阪)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] アミノリチオ化と炭素リチオ化の直結化学

    • Author(s)
      富岡清
    • Organizer
      富山大学理学部-有機合成化学協会共催特別講演会
    • Place of Presentation
      富山大学理学部(富山)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 医薬品プロセス化学の展望

    • Author(s)
      富岡清
    • Organizer
      「電磁波励起非平衡反応場の物理化学と産業応用」に関する先導的研究開発委員会
    • Place of Presentation
      東京工業大学蔵前会館(東京)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Book] Copper-Catalyzed Asymmetric Synthesis2014

    • Author(s)
      Kiyoshi Tomioka
    • Total Pages
      29
    • Publisher
      Wiley-VCH
    • Related Report
      2013 Research-status Report
  • [Book] Comprehensive Chirality, Volume 32012

    • Author(s)
      Kiyoshi Tomioka
    • Total Pages
      29
    • Publisher
      Elsevier
    • Related Report
      2012 Research-status Report
  • [Book] Comprehensive Chirality, Volume 42012

    • Author(s)
      Kiyoshi Tomioka
    • Total Pages
      10
    • Publisher
      Elsevier
    • Related Report
      2012 Research-status Report
  • [Remarks] 同志社女子大学 研究者データベース

    • URL

      http://research-db.dwc.doshisha.ac.jp/rd/html/japanese/researchersHtml/3239/3239_Researcher.html

    • Related Report
      2012 Research-status Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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