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Tandem bond forming reactions based on oxidative umpolung of organomeallic reagents

Research Project

Project/Area Number 23790029
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

YAMAMOTO YASUTOMO  同志社女子大学, 薬学部, 助教 (10452278)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords酸化 / 極性転換 / 多成分反応 / 複素環
Research Abstract

Oxidation of an anionic species to a radical or cationic species is an important umpolung methodology for changing the reactivity of anionic intermediates, and it is potentially useful in combination with anionic cascade reactions. An addition reaction of alkenylmagnesium bromide with p-toluenesulfonyl isocyanate and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated lactams in one pot. This oxidative halocyclization was also applicable to a one-pot synthesis of cyclic ether, cyclic amine, lactone, pyrazolidine using a aldehyde, imine, carbon dioxide, and azodicarboxylate, respectively.

Report

(5 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Products Report
  • Research Products

    (40 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (22 results) Book (4 results) Remarks (2 results)

  • [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 Annual Research Report 2013 Final Research 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 Annual Research 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 Annual Research Report 2013 Final Research 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
      2013 Final Research Report 2012 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] 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] High Performance of N-Alkoxycarbonyl-Imines in Triethylborane-Mediated Tin-Free Radical Addition2012

    • Author(s)
      Kiyoshi Tomioka
    • Journal Title

      J.Org.Chem.

      Volume: 77巻 Issue: 3 Pages: 1547-1553

    • DOI

      10.1021/jo2025042

    • Related Report
      2011 Research-status Report Products Report
    • Peer Reviewed
  • [Journal Article] Chiral N-Heterocyclic Carbene. Copper(I)-Catalyzed Asymmetric Allylic Arylation of Aliphatic Allylic Bromides : Steric and Electronic Effects on γ-Selectivity2011

    • Author(s)
      Selim, K. B.; Nakanishi, H.; Matsumoto, Y.; Yamamoto, Y.; Yamada, K.; Tomioka, K
    • Journal Title

      J. Org. Chem

      Volume: 76(5) Issue: 5 Pages: 1398-1408

    • DOI

      10.1021/jo102386s

    • Related Report
      2011 Research-status Report Products Report
    • Peer Reviewed
  • [Journal Article] Steric Influence of N-Phosphorus-arylimines on the Rhodium-Catalyzed Asymmetric Arylation2011

    • Author(s)
      Kiyoshi Tomioka
    • Journal Title

      Tetrahedron

      Volume: 67巻 Issue: 35 Pages: 6469-6473

    • DOI

      10.1016/j.tet.2011.06.033

    • Related Report
      2011 Research-status Report Products 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
      2011 Research-status Report Products Report
    • Peer Reviewed
  • [Presentation] Javaberine Aおよびepi-Javaberine Aの全合成2014

    • Author(s)
      山本康友
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      ホテル日航熊本(熊本県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] NMR studies on the structure of a lithium amide–chiral diether complex for an asymmetric reaction2013

    • Author(s)
      山本康友
    • Organizer
      The 23rd French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      長崎
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot Synthesis of N- Heterocycles by Tandem Carbamoylation- Oxidative Bromolactamization ofω- Alkenylmagnesiumbromide2013

    • Author(s)
      山本康友
    • Organizer
      12th Ibn Sina International Conference on Pure and Applied Heterocyclic Chemistry
    • Place of Presentation
      Luxol, Egypt
    • Related Report
      2013 Final Research Report
  • [Presentation] NMR studies on the structure of a lithium amide-chiral diether complex for an asymmetric reaction2013

    • Author(s)
      山本康友
    • Organizer
      The 23rd French-Japanese Symposium on Medicinal and Fine Chemistry (FJS-2013)
    • Place of Presentation
      ANAクラウンプラザホテル長崎グラバーヒル(長崎県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] One-pot Synthesis of N-Heterocycles by Tandem Carbamoylation-Oxidative Bromolactamization of ω-Alkenylmagnesiumbromide2013

    • Author(s)
      山本康友
    • Organizer
      12th IBN SINA conference 2013
    • Place of Presentation
      Sonesta Hotel (ルクソール)
    • Related Report
      2012 Research-status Report
  • [Presentation] リチウムアミド-キラルジエーテル複合反応剤のNMR構造2013

    • Author(s)
      山本康友
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(神奈川県)
    • Related Report
      2012 Research-status Report
  • [Presentation] アミノアルケンの分子内ヒドロアミノ化によるJavaberine Aの合成研究2012

    • Author(s)
      山本康友
    • Organizer
      日本プロセス化学会2012サマーシンポジウム
    • Place of Presentation
      京都テルサ(京都府)
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthetic Studies of Tetrahydroisoquinoline Alkaloids by an Intramolecular Hydroamination of Aminoalkenes2011

    • Author(s)
      山本康友
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      京王プラザホテル (東京都)
    • Year and Date
      2011-12-01
    • Related Report
      Products Report
  • [Presentation] One-pot synthesis of heterocycles by an addition of ω-alkenylmagnesium bromide to C=N, C=O and subsequent oxidation2011

    • Author(s)
      山本康友
    • Organizer
      10th International Symposium on Organic Reactions
    • Place of Presentation
      慶應義塾大学日吉キャンパス (神奈川県)
    • Year and Date
      2011-11-23
    • Related Report
      Products Report
  • [Presentation] ω-アルケニルGrignardのカルバモイル化-酸化的ブロモラクタム化による含窒素複素環のワンポット合成2011

    • Author(s)
      山本康友
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      あわぎんホール (徳島県)
    • Year and Date
      2011-11-08
    • Related Report
      Products Report
  • [Presentation] One-pot Synthesis of N-Heterocycles by Tandem Carbamoylation-Oxidative Bromolactamization of ω-Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 2nd International Symposium on Process Chemistry [ISPC 2011]
    • Place of Presentation
      京都国際会館(京都府)
    • Year and Date
      2011-08-11
    • Related Report
      Products Report
  • [Presentation] One-pot Synthesis of N-Heterocycles by Tandem Carbamoylation-Oxidative Bromolactamization of ω-Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Shanghai International Convention Center (中国・上海)
    • Year and Date
      2011-07-25
    • Related Report
      Products Report
  • [Presentation] ω-アルケニルGrignardのカルバモイル化-酸化的ブロモラクタム化による含窒素複素環のワンポット合成2011

    • Author(s)
      山本康友
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot synthesis of heterocycles by an addition ofω-alkenyl- magnesium bromide to C=N, C=O and subsequent oxidation2011

    • Author(s)
      山本康友
    • Organizer
      10th International Symposium on Organic Reactions [ISOR10]
    • Place of Presentation
      慶應大学
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot Synthesis of N- Heterocycles by Tandem Carbamoylation- Oxidative Bromolactamization ofω- Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 22nd French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Rouen, France
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot Synthesis of N- Heterocycles by Tandem Carbamoylation- Oxidative Bromolactamization ofω- Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 2nd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会館
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot Synthesis of N- Heterocycles by Tandem Carbamoylation- Oxidative Bromolactamization ofω- Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      IUPAC International Symposia on Organometallic Chemistry Directed Towards Organic Synthesis [OMCOS 16]
    • Place of Presentation
      Shanghai
    • Related Report
      2013 Final Research Report
  • [Presentation] One-pot Synthesis of N-Heterocycles by Tandem Carbamoylation-Oxidative Bromolactamization of ω-Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 2nd International Symposium on Process Chemistry [ISPC 2011]
    • Place of Presentation
      京都国際会館(京都府)
    • Related Report
      2011 Research-status Report
  • [Presentation] One-pot Synthesis of N-Heterocycles by Tandem Carbamoylation-Oxidative Bromolactamization of ω-Alkenylmagnesiumbromide2011

    • Author(s)
      山本康友
    • Organizer
      The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Shanghai International Convention Center(中国・上海)
    • Related Report
      2011 Research-status Report
  • [Presentation] One-pot synthesis of heterocycles by an addition of ω-alkenylmagnesium bromide to C=N, C=O and subsequent oxidation2011

    • Author(s)
      山本康友
    • Organizer
      10th International Symposium on Organic Reactions
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県)
    • Related Report
      2011 Research-status Report
  • [Presentation] ω-アルケニルGrignardのカルバモイル化-酸化的ブロモラクタム化による含窒素複素環のワンポット合成2011

    • Author(s)
      山本康友
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      あわぎんホール(徳島県)
    • Related Report
      2011 Research-status Report
  • [Presentation] Synthetic Studies of Tetrahydroisoquinoline Alkaloids by an Intramolecular Hydroamination of Aminoalkenes2011

    • Author(s)
      山本康友
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      京王プラザホテル(東京都)
    • Related Report
      2011 Research-status Report
  • [Book] Comprehensive Chirality Volume 32012

    • Author(s)
      山本康友
    • Publisher
      Elsevier
    • Related Report
      2013 Final Research Report
  • [Book] Comprehensive Chirality Volume 42012

    • Author(s)
      山本康友
    • Publisher
      Elsevier
    • Related Report
      2013 Final Research Report
  • [Book] Comprehensive Chirality, Volume 32012

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

    • Author(s)
      Yasutomo Yamamoto
    • Total Pages
      10
    • Publisher
      Elsevier
    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://research-db.dwc.doshisha.ac.jp/rd/html/japanese/researchersHtml/3247/3247_Researcher.html

    • Related Report
      2013 Final Research 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/3247/3247_Researcher.html

    • Related Report
      2012 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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