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Efficient Synthesis of Optically Active Halogenated Compounds with ?-Halocarbonyl Compounds

Research Project

Project/Area Number 21750096
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionToyohashi University of Technology

Principal Investigator

SHIBATOMI Kazutaka  Toyohashi University of Technology, 大学院・工学研究科, 助教 (00378259)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywords不斉合成・反応 / フッ素 / 塩素 / ハロゲン化 / 不斉触媒 / アミノ酸 / Diels-Alder反応 / オキサザボロリジン / ハロゲン / 不斉合成 / 光学活性化合物 / 不斉フッ素化反応 / ルイス酸
Research Abstract

Fluorinated organic molecules are known to be quite important in the synthesis of drugs and their candidates. Efficient synthetic methods for these compounds, especially having a fluorinated chiral carbon center, are strongly required. Here, we succeeded in asymmetric fluorination of alfa-chloro ketoester, and also succeeded in asymmetric Diels-Alder reaction of alfa-fluoro enone. These reactions afforded some new class of chiral fluorinated compounds with high optical purity. These compounds are expected to be useful building blocks for drug design.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (38 results)

All 2011 2010 2009 Other

All Journal Article (6 results) (of which Peer Reviewed: 5 results) Presentation (28 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] StereoselectiveConstruction of Halogenated QuaternaryStereogenic Centers via CatalyticAsymmetric Diels-Alder Reaction2010

    • Author(s)
      柴富一孝, 二木建太郎, 小林史人, 岩佐精二, 山本尚
    • Journal Title

      Journal of the American Chemical Society 132巻

      Pages: 5625-5627

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Alternative SyntheticStrategies for EnantioselectiveConstruction of Halogenated ChiralCarbon Centers2010

    • Author(s)
      柴富一孝
    • Journal Title

      Synthesis

      Pages: 2679-2702

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels-Alder Reaction2010

    • Author(s)
      柴富一孝, 二木建太郎, 小林史人, 岩佐精二, 山本尚
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 5625-5627

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alternative Synthetic Strategies for Enantioselective Construction of Halogenated Chiral Carbon Centers2010

    • Author(s)
      柴富一孝
    • Journal Title

      Synthesis

      Pages: 2679-2702

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex2010

    • Author(s)
      A.Abu-Elfotoh, K.Phomkeona, 柴富一孝, 岩佐精二
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 8439-8443

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 創薬を指向した光学活性フッ素化合物の新規合成法2010

    • Author(s)
      柴富一孝
    • Journal Title

      ケミカルエンジニヤリング VOL.55

      Pages: 198-203

    • Related Report
      2009 Annual Research Report
  • [Presentation] キラルオキサザボロリジン触媒を用いた不斉Diels-Alder反応によるトリフルオロメチル化合物の合成2011

    • Author(s)
      柴富一孝
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (震災のためWeb上での予稿公開のみ)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] ルイス酸触媒を用いたgem-クロロフルオロ化合物の不斉合成およびその立体特異的誘導化反応2011

    • Author(s)
      楢山輝(発表者), 柴富一孝(代表者)
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      (震災のためWeb上での予稿公開のみ)
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Stereoselective Synthesisof Fluorinated Cyclohexene Derivativesvia Asymmetric Diels-Alder Reaction2011

    • Author(s)
      柴富一孝
    • Organizer
      20th Winter Fluorine Conference
    • Place of Presentation
      フロリダ(米国)
    • Year and Date
      2011-01-12
    • Related Report
      2010 Final Research Report
  • [Presentation] Stereoselective Synthesis of Fluorinated Cyclohexene Derivatives via Asymmetric Diels-Alder Reaction2011

    • Author(s)
      柴富一孝
    • Organizer
      20th Winter Fluorine Conference
    • Place of Presentation
      フロリダ(米国)
    • Year and Date
      2011-01-12
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective Construction of Fluorinated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels-Alder Reaction2010

    • Author(s)
      柴富一孝
    • Organizer
      Pacifichem-2010
    • Place of Presentation
      ホノルル(ハワイ)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Final Research Report
  • [Presentation] Novel Spiro Chiral Oxazoline Ligands for Asymmetric Catalysis2010

    • Author(s)
      楢山輝(発表者), 柴富一孝(代表者)
    • Organizer
      Pacifichem-2010
    • Place of Presentation
      ホノルル(ハワイ)(米国)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective Construction of Fluorinated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels-Alder Reaction2010

    • Author(s)
      柴富一孝
    • Organizer
      Pacifichem-2010
    • Place of Presentation
      ホノルル(ハワイ)(米国)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] フッ素化された不斉炭素の高立体選択的構築法2010

    • Author(s)
      柴富一孝
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知) 招待講演
    • Year and Date
      2010-11-06
    • Related Report
      2010 Final Research Report
  • [Presentation] フッ素化された不斉炭素の高立体選択的構築法2010

    • Author(s)
      柴富一孝
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知)(招待講演)
    • Year and Date
      2010-11-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] 活性メチレン化合物の不斉クロロフルオロ化反応2010

    • Author(s)
      楢山輝(発表者), 柴富一孝(代表者)
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知)
    • Year and Date
      2010-11-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不斉Diels-Alder反応によるフルオロシクロヘキセンの高エナンチオ選択的合成法2010

    • Author(s)
      小林史人(発表者), 柴富一孝(代表者)
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知)
    • Year and Date
      2010-11-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] キラル銅触媒を用いたβ-ケトエステル類の高エナンチオ選択的塩素化反応2010

    • Author(s)
      曽我宜賀(発表者), 柴富一孝(代表者)
    • Organizer
      第41回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      豊橋技術科学大学(愛知)
    • Year and Date
      2010-11-06
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不斉Diels-Alder反応によるフッ素化シクロヘキセン誘導体の立体選択的合成2010

    • Author(s)
      柴富一孝
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインク愛知(名古屋)
    • Year and Date
      2010-11-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] フルオロオレフィンをジエノフィルとする不斉Diels-Alder反応2010

    • Author(s)
      柴富一孝
    • Organizer
      第34回フッ素化学討論会
    • Place of Presentation
      札幌サンプラザ コンサートホール(札幌)
    • Year and Date
      2010-10-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Fluorinated Cyclohexene Derivatives via Combined Acid-Catalyzed Diels-Alder Reaction2010

    • Author(s)
      柴富一孝
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学(東京)
    • Year and Date
      2010-09-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Enantioselective Construction of Fluorinated Chiral Carbon Centers2010

    • Author(s)
      柴富一孝
    • Organizer
      BIT's 1st Annual WorldCongress of Catalytic AsymmetricSynthesis 2010
    • Place of Presentation
      北京(中国)
    • Year and Date
      2010-05-21
    • Related Report
      2010 Final Research Report
  • [Presentation] Enantioselective Construction of Fluorinated Chiral Carbon Centers2010

    • Author(s)
      柴富一孝
    • Organizer
      BIT's 1st Annual World Congress of Catalytic Asymmetric Synthesis 2010
    • Place of Presentation
      北京(中国)
    • Year and Date
      2010-05-21
    • Related Report
      2010 Annual Research Report
  • [Presentation] gem-クロロフルオロ化合物の不斉合成2010

    • Author(s)
      柴富一孝
    • Organizer
      第8回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京)
    • Year and Date
      2010-05-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] 高エナンチオ選択的Diels-Alder反応によるフッ素化不斉四級炭素の構築2010

    • Author(s)
      小林史人, 柴富一孝, 岩佐精二, 山本尚
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Highly Enantiose lective Synthesis of α, α -Chlorofluoro Carbonyl Compounds2009

    • Author(s)
      柴富一孝
    • Organizer
      11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都)
    • Year and Date
      2009-11-12
    • Related Report
      2010 Final Research Report
  • [Presentation] Highly Enantioselective Synthesis of α,α-Chlorofluoro Carbonyl Compounds2009

    • Author(s)
      柴富一孝, 楢山輝, 小林史人, 武藤翼, 岩佐精二
    • Organizer
      11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都市)
    • Year and Date
      2009-11-12
    • Related Report
      2009 Annual Research Report
  • [Presentation] ルイス酸触媒を用いたアルカン類のC-Hハロゲン化反応2009

    • Author(s)
      中村奈美, 柴富一孝, 岩佐精二
    • Organizer
      第40回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜大学(岐阜市)
    • Year and Date
      2009-11-08
    • Related Report
      2009 Annual Research Report
  • [Presentation] スピロ型キラルオキサゾリン配位子を利用したα,α-クロロフルオロ化合物の触媒的不斉合成2009

    • Author(s)
      楢山輝, 小林史人, 曽我宜賀, 柴富一孝, 岩佐精二
    • Organizer
      第33回フッ素化学討論会
    • Place of Presentation
      八王子学園都市センター(八王子市)
    • Year and Date
      2009-10-20
    • Related Report
      2009 Annual Research Report
  • [Presentation] Lewis Acid-Catalyzed Asymmetric α-Halogenation of Carbonyl Compounds2009

    • Author(s)
      柴富一孝
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Lewis Acid-Catalyzed Asymmetric α-Halogenation of Carbonyl Compounds2009

    • Author(s)
      柴富一孝, 楢山輝, 小林史人, 岩佑精二
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都市)
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] 有機分子の高選択的ハロゲン化反応の開拓2009

    • Author(s)
      柴富一孝
    • Organizer
      有機合成化学協会東海支部「若手研究者のためのセミナー)
    • Place of Presentation
      静岡県立大学(静岡市) 招待講演
    • Year and Date
      2009-07-18
    • Related Report
      2010 Final Research Report
  • [Presentation] 有機分子の高選択的ハロゲン化反応の開拓2009

    • Author(s)
      柴富一孝
    • Organizer
      有機合成化学協会東海支部「若手研究者のためのセミナー」(招待公演)
    • Place of Presentation
      静岡県立大学(静岡市)
    • Year and Date
      2009-07-18
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光学活性スピロオキサゾリン配位子を用いた活性メチン化合物の触媒的不斉塩素化反応2009

    • Author(s)
      曽我宜賀, 柴富一孝, 岩佐精二
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学(大阪市)
    • Year and Date
      2009-03-28
    • Related Report
      2009 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://material.tutms.tut.ac.jp/STAFF/SHIBATOMI/pub.html.ja

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://material.tutms.tut.ac.jp/STAFF/SHIBATOMI/pub.html.ja

    • Related Report
      2010 Annual Research Report
  • [Patent(Industrial Property Rights)] 光学活性シクロヘキセン誘導体の製造方法、光学活性シクロヘキセン誘導体、並びにそれを用いた光学活性シクロヘキサジエン誘導体の製造方法及び光学活性シクロヘキサジエン誘導体2010

    • Inventor(s)
      柴富一孝,松村靖
    • Industrial Property Rights Holder
      豊橋技術科学大学,旭硝子株式会社
    • Industrial Property Number
      2010-233758
    • Filing Date
      2010-10-18
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] 光学活性シクロヘキセン誘導体の製造方法、光学活性シクロヘキセン誘導体、並びにそれを用いた光学活性シクロヘキサジエン誘導体の製造方法及び光学活性シクロヘキサジエン誘導体2010

    • Inventor(s)
      柴富一孝, 松村靖
    • Industrial Property Rights Holder
      豊橋技術科学大学, 旭硝子株式会社
    • Industrial Property Number
      2010-233758
    • Filing Date
      2010-10-18
    • Related Report
      2010 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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