• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Novel cascade reactions triggered by silyl acetal activation

Research Project

Project/Area Number 26460015
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

Yanai Hikaru  東京薬科大学, 薬学部, 准教授 (10408685)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords有機化学 / シリルアセタール / ブレンステッド酸 / 多環式芳香族化合物 / カスケード反応 / 多環式芳香族炭化水素 / 連続反応 / ナフタレン
Outline of Final Research Achievements

By using our own acid catalysts, we recently found that some silyl acetals were easily formed. On the basis of this finding, we developed some novel cascade reactions induced by treatment of the silyl acetals with fluoride sources. In particular, silyl acetals derived from 4-alkynylisocoumarine derivatives produced 1,2,3,4-tetrasubstitued naphthalenes in a highly regioselective manner.
Our naphthalene synthesis is the two-step reaction; 1) acidic zwitterion-induced addition of ketene silyl acetal to lactonic carbonyl group, and 2) fluoride-triggered ring-rearrangement reaction. In the first step, a notably high level of chemoselectivity was observed. This is an important advantage to realize a wide range of application scope for the present methodology.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (18 results)

All 2017 2016 2015 2014 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 3 results) Presentation (11 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results) Book (1 results) Remarks (3 results)

  • [Journal Article] Sequential Mukaiyama-Michael reaction induced by carbon acids2016

    • Author(s)
      Yanai, H., Kobayashi, O., Takada, K., Isono, T., Satoh, T.,Matsumoto, T.
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 16 Pages: 3280-3283

    • DOI

      10.1039/c5cc10115h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1,2,3,4-tetrasubstituted naphthalenes through a cascade reaction triggered by silyl acetal activation2016

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 51 Pages: 7974-7977

    • DOI

      10.1039/c6cc03510h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chemoselective Two-directional Reaction of Bi-functionalized Substrates: Formal Ketal-selective Mukaiyama Aldol Type Reaction2015

    • Author(s)
      Hikaru Yanai
    • Journal Title

      Synlett

      Volume: 26 Issue: 17 Pages: 2457-2461

    • DOI

      10.1055/s-0035-1560478

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 日本薬学会 第137年会2017

    • Author(s)
      矢内 光
    • Organizer
      温和な酸触媒を用いた二種のケトン間における化学選択性
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Annual Research Report
  • [Presentation] 強酸性炭素酸誘導体を用いたイソクマリン類とケテンシリルアセタールの反応2016

    • Author(s)
      矢内 光
    • Organizer
      第42回 反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡
    • Year and Date
      2016-11-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] ビス(ペルフオロアキスホニペル)アルカン類の合成と有機溶媒中での酸性度評価2016

    • Author(s)
      矢内 光
    • Organizer
      第39回 フッ素化学討論会
    • Place of Presentation
      佐賀
    • Year and Date
      2016-09-29
    • Related Report
      2016 Annual Research Report
  • [Presentation] カルボアニオン構造をもつピリジニウム型双性イオンの合成と利用法2016

    • Author(s)
      矢内 光
    • Organizer
      第109回 有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2016-06-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] Highly Selective Synthesis of 1,2,3,4-Tetrasubstituted Naphthalenes Through Fluoride-induced Cascade Reaction2016

    • Author(s)
      Hikaru Yanai
    • Organizer
      25th French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      Tokyo
    • Year and Date
      2016-05-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] 溶媒効果に基づくMukaiyamaアルドール型反応の化学選択性のスイッチング2016

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-29
    • Related Report
      2015 Research-status Report
  • [Presentation] 酸性双性イオン触媒を用いた Mukaiyama アルドール反応の化学選択性2016

    • Author(s)
      矢内 光
    • Organizer
      第60回 日本薬学会 関東支部大会
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
  • [Presentation] Chemoselective Two-directional Reaction Induced by Acidic Zwitterions Bearing Highly Stabilized Carbanion Moiety2015

    • Author(s)
      Hikaru Yanai
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 新しい有機酸触媒の開発:有機フッ素化学からのアプローチ2015

    • Author(s)
      矢内 光
    • Organizer
      フルオラス科学研究会 第8回 シンポジウム
    • Place of Presentation
      静岡
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] シリルアセタールの活性化を引き金とする1,2,3,4-四置換ナフタレンの選択的な合成2015

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] フッ素の特異性に着目した有機フッ素化合物の新しい合成法とその利用2015

    • Author(s)
      矢内 光
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
    • Invited
  • [Book] Green Synthetic Approaches for Biologically Relevant Heterocycles2014

    • Author(s)
      Hikaru Yanai
    • Publisher
      Elsevier
    • Related Report
      2014 Research-status Report
  • [Remarks] 研究グループのホームページ

    • URL

      http://www.ps.toyaku.ac.jp/wp/Org_Synth/

    • Related Report
      2016 Annual Research Report
  • [Remarks]

    • URL

      http://www.ps.toyaku.ac.jp/wp/Org_Synth/

    • Related Report
      2015 Research-status Report
  • [Remarks] http://www.ps.toyaku.ac.jp/wp/Org_Synth/?p=574

    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi