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Development of Enantioselective Hydroalumination and Its Application to Asymmetric Synthesis of Chiral tert-Alcohol

Research Project

Project/Area Number 18750081
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyushu University (2007-2008)
Tokyo Institute of Technology (2006)

Principal Investigator

IGAWA Kazunobu  Kyushu University, 先導物質化学研究所, 助教 (80401529)

Project Period (FY) 2006 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥4,150,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥150,000)
Fiscal Year 2008: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2007: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2006: ¥3,000,000 (Direct Cost: ¥3,000,000)
Keywords不斉合成 / キラル3級アルコール / ヒドロアルミニウム化反応 / オゾン酸化 / 有機合成 / アルケニルシラン / 不斉ケイ素 / 学活性アルコール / 有機化学 / 光学活性3級アルコール / シリルペルオキシ化合物 / キラルポリオール
Research Abstract

生理活性物質や機能性材料,不斉合成反応剤の部分構造もしくは,それらの合成原料として重要なキラル三級アルコールの効率的な不斉合成法となる,アキラルなビスアルキニルカルビノールの不斉非対称化を伴う,エナンチオ選択的ヒドロアルミニウム化反応の開発に成功した.また,その研究過程において,これまで全く報告例のないアルケンの付加型オゾン酸化反応を見出し,本オゾン酸化反応をエナンチオ選択的ヒドロアルミニウム化反応と組み合わせて用いる,キラルポリオール類の新規不斉合成法の開発に成功した.

Report

(4 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (24 results)

All 2009 2008 2007 2006 Other

All Journal Article (6 results) (of which Peer Reviewed: 2 results) Presentation (15 results) Remarks (3 results)

  • [Journal Article] Partial Oxydation of Alkenylsilane with Ozone : A Novel Stereoselective Approach for the Diol- and Triol-derivatives2008

    • Author(s)
      Igawa Kazunobu ; Sakita Kyohei ; Murakami Masanori ; Tomooka Katsuhiko
    • Journal Title

      Synthesis

      Pages: 1641-1645

    • Related Report
      2008 Final Research Report
  • [Journal Article] Enantioselective Synthesis of Silanol2008

    • Author(s)
      K. Igawa, et.al.
    • Journal Title

      J. Am. Chem. Soc 130

      Pages: 16132-16133

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Partial Oxidation of Alkenylsilanes with Ozone: A Novel Stereoselective Approach to the Diol and Triol Derivatives2008

    • Author(s)
      K., Igawa, et. al.
    • Journal Title

      Synthesis (in press)

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Oxy-Functionalization of γ-Silyl Allylic Alcohols with Ozone : A Facile Synthesis of Silyl Peroxide and Its Reactions2006

    • Author(s)
      Murakami Masanori ; Sakita Kyohei ; Igawa Kazunobu ; Tomooka Katsuhiko
    • Journal Title

      Org. Lett 8

      Pages: 4023-4026

    • Related Report
      2008 Final Research Report
  • [Journal Article] Anionic Ring-Enlarging Reaction of a Hemiaminal System : Stereoselective Approach to Disubstituted Tetrahydroisoquinolone2006

    • Author(s)
      Katsuhiko Tomooka, Takahiro Tomoyasu, Takayuki Hanji, Kazunobu Igawa
    • Journal Title

      SYNLETT 15

      Pages: 2449-2453

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Stereoselective Oxy-Functionalization of γ-Silyl Allylic Alcohols with Ozone : A Facile Synthesis of Silyl Peroxide and Its Reactions2006

    • Author(s)
      Masanori Murakami, Kyohei Sakita, Kazunobu Igawa, Katsuhiko Tomooka
    • Journal Title

      Organic Letters 8・18

      Pages: 4023-4026

    • Related Report
      2006 Annual Research Report
  • [Presentation] アルケニルシランのオゾン酸化 : カルボキシシランエステルの新規合成法2009

    • Author(s)
      井川和宣,古閑直人,友岡克彦
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-29
    • Related Report
      2008 Final Research Report
  • [Presentation] アルケニルシランのオゾン酸化 : 置換基効果の精査2009

    • Author(s)
      河崎悠也,井川和宣,友岡克彦
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2009-03-29
    • Related Report
      2008 Final Research Report
  • [Presentation] Enantioselective Synthesis of Chiral Silanol : Asymmetric Nucleophilic Substitution Reaction of Achiral Dialkoxysilane2008

    • Author(s)
      K. Igawa, et.al.
    • Organizer
      Organic & Polymer Materials for Ubiquitous ICT
    • Place of Presentation
      九州大学筑紫キャンパス
    • Year and Date
      2008-12-21
    • Related Report
      2008 Annual Research Report
  • [Presentation] A Novel Facet of Ozone Oxidation : Addition-type Oxidation of Alkene2008

    • Author(s)
      Igawa Kazunobu ; Murakami Masanori ; Sakita Kyohei ; Kawasaki Yuuya ;Tomooka Katsuhiko
    • Organizer
      The 9th International Symposium on Organic Reactions
    • Place of Presentation
      台湾
    • Year and Date
      2008-11-22
    • Related Report
      2008 Final Research Report
  • [Presentation] A Novel Facet of Ozone Oxidation : Addition-type Oxidation of Alkene2008

    • Author(s)
      K. Igawa, et.al.
    • Organizer
      The 9th International Symposium on Organic Reactions
    • Place of Presentation
      Chiayi, Taiwan
    • Year and Date
      2008-11-22
    • Related Report
      2008 Annual Research Report
  • [Presentation] アルケンの新規付加型酸化 : アルケニルシランのオゾン酸化2008

    • Author(s)
      井川和宣,崎田享平,村上正徳,河崎悠也,友岡克彦
    • Organizer
      第50回天然有機化合物討論会
    • Place of Presentation
      福岡
    • Year and Date
      2008-10-01
    • Related Report
      2008 Final Research Report
  • [Presentation] アルケンの新規付加型酸化 ; アルケニルシランのオゾン酸化2008

    • Author(s)
      井川和宣, 他
    • Organizer
      第50回天然有機化合物討論会
    • Place of Presentation
      福岡国際会議場
    • Year and Date
      2008-10-01
    • Related Report
      2008 Annual Research Report
  • [Presentation] 新規なオゾン酸化 : アルケニルシランの付加型酸化2008

    • Author(s)
      河崎悠也,崎田享平,村上正徳,井川和宣,友岡克彦
    • Organizer
      第45回化学関連支部合同九州大会
    • Place of Presentation
      福岡
    • Year and Date
      2008-07-05
    • Related Report
      2008 Final Research Report
  • [Presentation] 新規なオゾン酸化 : アルケニルシランの付加型酸化2008

    • Author(s)
      井川和宣, 他
    • Organizer
      第45回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2008-07-05
    • Related Report
      2008 Annual Research Report
  • [Presentation] アルケニルシランのオゾン酸化 : 置換基効果の精査2008

    • Author(s)
      井川和宣, 他
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2008-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] アルケニルシランのオゾン酸化 : カルボキシシランエステルの新規合成法2008

    • Author(s)
      井川和宣, 他
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2008-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] アルケニルシランのオゾン酸化 : α-シリルペルオキシケトンの合成とその反応2008

    • Author(s)
      河崎悠也,井川和宣,友岡克彦
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-27
    • Related Report
      2008 Final Research Report
  • [Presentation] アルケニルシランのオゾン酸化:α-シリルペルオキシケトンの合成とその反応2008

    • Author(s)
      河崎 悠也, 井川 和宣, 友岡 克彦
    • Organizer
      日本化学会 第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] オゾンによるγ-シリルアリルアルコールの立体選択的な酸素官能基化2007

    • Author(s)
      崎田享平,村上正徳,井川和宣,友岡克彦
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2007-03-27
    • Related Report
      2008 Final Research Report
  • [Presentation] Enantioselective Hydroalumination of Prochiral Propargylic Alcohol : An Efficient Stereoselective Approach to Functionalized Chiral tert-Alcohol2006

    • Author(s)
      Igawa Kazunobu ; Murakami Masanori ; Tomooka Katsuhiko
    • Organizer
      ICOB-5 & ISCNP-25 IUPAC International Conference on Bioactiversity and Natural Product
    • Place of Presentation
      京都
    • Year and Date
      2006-07-25
    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://www.cm.kyushu-u.ac.jp/tomooka/tomooka/Top%20Page.html

    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://www.cm.kyushu-u.ac.jp/

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.cm.kyushu-u.ac.jp/tomooka/tomooka/Top%20Page.html

    • Related Report
      2008 Annual Research Report

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Published: 2006-04-01   Modified: 2016-04-21  

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