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Catalytic Asymmetric Synthesis of Silicon-Stereogenic Organosilanes

Research Project

Project/Area Number 24750089
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

SHINTANI RYO  東京大学, 工学(系)研究科(研究院), 准教授 (50372561)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords不斉ケイ素中心 / 不斉ゲルマニウム中心 / 触媒的不斉合成 / 非対称化反応 / ロジウム / パラジウム / 付加環化反応
Research Abstract

Optically active compounds constitute an important class in various field of research, and the development of efficient synthetic methods for optically active compounds has been extensively investigated to date. But most of them are directed toward the synthesis of organic compounds possessing carbon stereocenters. In contrast, catalytic asymmetric synthesis of silicon-stereogenic organisilanes has been much less explored. In this context, I worked on the development of new asymmetric catalyses involving desymmetrization of organosilicon compounds. As a result, optically active organosilanes such as dibenzosiloles and dibenzooxasilines became easily accessible.

Report

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

    (25 results)

All 2014 2013 2012 2011 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (14 results) (of which Invited: 1 results)

  • [Journal Article] Asymmetric Hydrosilylation of Cyclohexa-1,3-diene with Trichlorosilane by Palladium Catalysts Coordinated with Chiral Phosphoramidite Ligands2013

    • Author(s)
      Park, H. S.; Han, J. W.; Shintani, R.; Hayashi, T.
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 24 Issue: 7 Pages: 418-420

    • DOI

      10.1016/j.tetasy.2013.02.002

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Hydroboration of Carbon Dioxide2013

    • Author(s)
      Shintani, R.; Nozaki, K.
    • Journal Title

      Organometallics

      Volume: 32 Issue: 8 Pages: 2459-2462

    • DOI

      10.1021/om400175h

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of α-Tri- and α-Tetrasubstituted Allylsilanes by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Silylboronates2013

    • Author(s)
      Takeda, M.; Shintani, R.; Hayashi, T.
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 10 Pages: 5007-5017

    • DOI

      10.1021/jo400888b

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Catalyst Removal and Recycling in Copolymerization of Epoxides with Carbon Dioxide via Simple Liquid–Liquid Phase Separation2013

    • Author(s)
      Nakano, K.; Fujie, R.; Shintani, R.; Nozaki, K.
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 81 Pages: 9332-9334

    • DOI

      10.1039/c3cc45622f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzooxasilines via Enantioselective Transmetalation2012

    • Author(s)
      Shintani, R. ; Maciver, E. E. ; Tamakuni, F. ; Hayashi, T.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 41 Pages: 16955-16958

    • DOI

      10.1021/ja3076555

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes : Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations2012

    • Author(s)
      新谷亮, 守屋孝平, 林民生
    • Journal Title

      Org. Lett.

      Volume: 14巻 Pages: 2902-2905

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C–H Bond Functionalization2012

    • Author(s)
      新谷亮, 大伴晴香, 太田健介, 林民生
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134巻 Issue: 17 Pages: 7305-7308

    • DOI

      10.1021/ja302278s

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Synthesis of 4-Oxasprio[2.4]heptanes via Central Attack of Oxygen Nucleophiles to pi-Allylpalladium Intermediates2012

    • Author(s)
      Shintani, R.; Ito, T.; Hayashi, T.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 9 Pages: 2410-2413

    • DOI

      10.1021/ol300852v

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations2012

    • Author(s)
      Shintani, R.; Moriya, K.; Hayashi, T.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 11 Pages: 2902-2905

    • DOI

      10.1021/ol301191u

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed asymmetric synthesis of 2-pyrrolidionones with a quaternary carbon stereocenter2012

    • Author(s)
      Shintani, R.; Ito, T.; Nagamoto, M.; Otomo, H.; Hayashi, T.
    • Journal Title

      Chem. Commun.

      Volume: 48 Issue: 79 Pages: 9936-9938

    • DOI

      10.1039/c2cc35259a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Enantioselective Desymmetrization of Silacylobutanes : Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter2011

    • Author(s)
      Shintani, R.; Moriya, K.; Hayashi, T.
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 133 Issue: 41 Pages: 16440-16443

    • DOI

      10.1021/ja208621x

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] ロジウム触媒による不斉ケイ素中心を持つ光学活性ジベンゾシロールの合成2014

    • Author(s)
      高木智博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Year and Date
      2014-03-29
    • Related Report
      2013 Final Research Report
  • [Presentation] 銅/NHC触媒を用いた新しい不斉合成反応2014

    • Author(s)
      Shintani, R.
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学(熊本)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 銅触媒によるγ位二置換リン酸アリル類のアリールおよびシリルボロン酸エステルを用いた不斉アリル位置換反応2014

    • Author(s)
      Takeda, M.; Takatsu, K.; Shintani, R.; Hayashi, T.
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ロジウム触媒を用いた3-アリールシクロプロペンの重合反応2014

    • Author(s)
      Iino, R.; Shintani, R.; Nozaki, K.
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ロジウム触媒による不斉ケイ素中心を持つ光学活性ジベンゾシロールの合成2014

    • Author(s)
      Takagi, C.; Ito, T.; Shintani, R.; Nozaki, K.
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 不斉ケイ素中心を持つ架橋ビアリール化合物の触媒的不斉合成2013

    • Author(s)
      新谷亮
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] Enantioselective Synthesis of Allylsilanes by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Silylboronates2013

    • Author(s)
      Takeda, M.; Shintani, R.; Hayashi, T.
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学(東京)
    • Related Report
      2013 Annual Research Report
  • [Presentation] パラジウム触媒による不斉ケイ素中心を持つジベンゾシロールの不斉合成2012

    • Author(s)
      新谷亮
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学(大阪)
    • Year and Date
      2012-09-15
    • Related Report
      2013 Final Research Report
  • [Presentation] パラジウム触媒による環状有機化合物の高選択的合成法

    • Author(s)
      新谷 亮
    • Organizer
      第23回万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター(宮城)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒による不斉ケイ素中心をもつジベンゾシロールの不斉合成

    • Author(s)
      新谷 亮
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学(大阪)
    • Related Report
      2012 Research-status Report
  • [Presentation] 不斉ケイ素中心を持つ架橋ビアリール化合物の触媒的不斉合成

    • Author(s)
      新谷 亮
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Research-status Report
  • [Presentation] Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl- and Alkenylboronates

    • Author(s)
      竹田桃太郎
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都リーガロイヤルホテル(京都)
    • Related Report
      2012 Research-status Report
  • [Presentation] 銅触媒を用いたリン酸アリル類のシリルボロン酸エステルによる不斉アリル位置換反応

    • Author(s)
      竹田桃太郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Research-status Report
  • [Presentation] エポキシドー二酸化炭素交互共重合における触媒の回収および再利用

    • Author(s)
      藤江竜平
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Related Report
      2012 Research-status Report

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

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