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Stereochemical Study on Chiral Silicon Radical and Its Application for Novel Asymmetric Synthesis

Research Project

Project/Area Number 16K13955
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKyushu University

Principal Investigator

Tomooka Katsuhiko  九州大学, 先導物質化学研究所, 教授 (70207629)

Co-Investigator(Renkei-kenkyūsha) IGAWA Kazunobu  九州大学, 先導物質化学研究所, 助教 (80401529)
Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機合成化学 / 不斉ケイ素化学 / ラジカル反応 / 不斉合成
Outline of Final Research Achievements

To explore a chemistry of chiral silicon radical, we examined asymmetric synthesis of radical precursors and reactions. As result, we have developed highly stereoselective approach to chiral hydrosilanes based on, a) nucleophilic substitution reaction of alkoxysilane and organometallic reagent, and, b) asymmetric beta-elimination of silacyclopenteneoxide. And we accomplished stereoselective preparation of chiral silicon radicals from the hydrosilanes.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (16 results)

All 2018 2017 2016

All Journal Article (3 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (12 results) (of which Int'l Joint Research: 3 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of Stereoselectively Functionalized Silacyclopentanes2017

    • Author(s)
      Igawa Kazunobu、Tomooka Katsuhiko、Kuroo Akihiro、Yoshihiro Daisuke、Yamanaka Yuki
    • Journal Title

      Synlett

      Volume: 28 Issue: 18 Pages: 2445-2448

    • DOI

      10.1055/s-0036-1590826

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemistry of Chiral Silicon Molecule2017

    • Author(s)
      Igawa Kazunobu、Tomooka Katsuhiko
    • Journal Title

      Kagaku

      Volume: 72 Pages: 12-16

    • Related Report
      2017 Annual Research Report
  • [Journal Article] キラルケイ素分子の化学-地球上に存在しなかったキラル分子をつくりだす2017

    • Author(s)
      井川和宣,友岡和宣
    • Journal Title

      化学(2月号)

      Volume: 72 Pages: 12-16

    • NAID

      40021068026

    • Related Report
      2016 Research-status Report
    • Acknowledgement Compliant
  • [Presentation] キラルアルコキシシランに対する有機金属反応剤の求核置換反応2018

    • Author(s)
      井川和宣,野崎素良,高田純子,重松和樹,宮坂祥司,友岡克彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ヘテロ官能基化キラルシラシクロペンタン類の不斉合成2018

    • Author(s)
      黒尾明弘,井川和宣,友岡 克彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラルシラシクロペンテノールの立体選択的変換2017

    • Author(s)
      井川和宣, 吉廣大佑, 黒尾明弘, 友岡克彦
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大(神奈川)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 多官能基化されたキラルシラシクロペンタン類の立体選択的合成2017

    • Author(s)
      井川和宣,黒尾明弘,吉廣大佑,友岡克彦
    • Organizer
      第4回中分子戦略若手シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] キラルシラシクロペンタンの不斉合成と反応2017

    • Author(s)
      井川和宣,吉廣大佑,黒尾明弘,安部雄介,友岡克彦
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 立体選択的アリル位置換反応を鍵とするキラルシラシクロペンテノールの高度官能基化2017

    • Author(s)
      井川和宣,黒尾明弘,吉廣大佑,友岡克彦
    • Organizer
      第54回化学関連支部合同九州大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Silacyclopentanes2016

    • Author(s)
      Kazunobu Igawa, Daisuke Yoshihiro, Yusuke Abe, and Katsuhiko Tomooka
    • Organizer
      Asian Core Program 2016 Korea
    • Place of Presentation
      大田(韓国)
    • Year and Date
      2016-10-27
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 官能基化されたキラルシラシクロペンタン類の不斉合成2016

    • Author(s)
      井川和宣,吉廣大佑,安部雄介, 黒尾明弘,友岡克彦
    • Organizer
      第32回若手化学者のための化学道場
    • Place of Presentation
      にぎたつ会館(愛媛)
    • Year and Date
      2016-08-25
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric Ozone Oxidation of Silylalkene Using Chiral Silyl Auxiliary2016

    • Author(s)
      Yuuya Kawasaki, Kosuke Nishino, Naoto Mitsuda, Kazunobu Igawa, Katsuhiko Tomooka
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      Convention Center(大阪)
    • Year and Date
      2016-04-20
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Divergent Asymmetric Synthesis of Chiral Organosilanes: Enantioselective Synthesis of Chiral Silanols and Stereospecific Transformations Thereof2016

    • Author(s)
      Kazunobu Igawa, Junko Takada, Daisuke Yoshihiro, Naoto Kokan, Nobumasa Ichikawa, Tomohiro Shimono, Katsuhiko Tomooka
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      Convention Center(大阪)
    • Year and Date
      2016-04-20
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルジアルコキシシランの求核置換反応2016

    • Author(s)
      井川和宣,重松和樹,友岡克彦
    • Organizer
      第53回 化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場(福岡)
    • Related Report
      2016 Research-status Report
  • [Presentation] キラルジアルコキシシランの立体選択的求核置換反応2016

    • Author(s)
      井川和宣, 重松和樹, 友岡克彦
    • Organizer
      有機合成化学協会九州山口支部 2016第28回若手研究者のためのセミナー
    • Place of Presentation
      九州大学(福岡)
    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] 化合物又はその薬理学上許容される塩、光学活性体、医薬組成物、及び化合物の製造方法2018

    • Inventor(s)
      友岡克彦,井川和宣,黒尾明弘,吉廣大佑
    • Industrial Property Rights Holder
      友岡克彦,井川和宣,黒尾明弘,吉廣大佑
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-032202
    • Filing Date
      2018
    • Related Report
      2017 Annual Research Report

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Published: 2016-04-21   Modified: 2019-03-29  

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