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Construction of Polycycles via Hydrogen Shift MediatedC(s p 3)-H bond functionalization.

Research Project

Project/Area Number 22750044
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionGakushuin University

Principal Investigator

MORI Keiji  学習院大学, 理学部化学科, 助教 (10515076)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2010: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords水素転位 / C-H結合官能基化 / 多環骨格 / C-H結合活性化
Research Abstract

Whereasa range of related reactions of heteroatom-containing substrates (X = NR^2 or O) have been reported, the corresponding carbon analogue (X=CH2) had been overlooked until quite recently. We have disclosed that the benzylic C-H bond without an adjacent heteroatom could also participate in this type of transformation by selection of barbiturate as a electrophilic moiety, and the corresponding 3-aryltetraline derivatives were obtained in excellent chemical yield. Furthermore, we found thatt h I s reaction could be applied to an aliphatic substrates (without electronic assistance of adjacent heteroatom and arene).The asymmetric version of this type of reaction was also achieved by use of chiral phosphoric acid catalyst derived from BINOL. The synthetically useful tetrahydroquinoline derivatives were obtained with excellent enanioselectivities (over 90% ees).

Report

(3 results)
  • 2012 Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (24 results)

All 2012 2011 2010 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (13 results) (of which Invited: 4 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp3)-H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine2012

    • Author(s)
      Mori, K.; Kawasaki, T.; Akiyama, T
    • Journal Title

      Org. Lett

      Volume: 14 Issue: 6 Pages: 1436-1439

    • DOI

      10.1021/ol300180w

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rapid Access to 3-Aryltetraline Skeleton via C(sp3)-H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C-H Bondin Hydride Shift/Cyclization Sequence2011

    • Author(s)
      Mori, K.; Sueoka, S.; Akiyama, T
    • Journal Title

      Chem. Lett

      Volume: 40 Issue: 12 Pages: 1386-1388

    • DOI

      10.1246/cl.2011.1386

    • NAID

      130004426122

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Activation of Enantiotopic C(sp3)-Hydrogen by Means of Chiral Phosphoric Acid: Asymmetric Synthesis of Tetrahydroquinoline Derivatives2011

    • Author(s)
      Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J
    • Journal Title

      Am. Chem. Soc

      Volume: 133 Issue: 16 Pages: 6166-6169

    • DOI

      10.1021/ja2014955

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Expeditious Construction of a Carbobicyclic Skeleton via a sp3-C-H Functionalization: Hydride Shift from an Aliphatic Tertiary Position in an Internal Redox Process2011

    • Author(s)
      Mori, K.; Sueoka, S.; Akiyama T
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Issue: 8 Pages: 2424-2426

    • DOI

      10.1021/ja110520p

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Expeditious Constmction of Carbobicyclic Skeleton via sp^3 C-H Functionalization : Hydride Shift from Aliphatic Tertiary Position in Internal Redox Proccess2011

    • Author(s)
      森啓二
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Pages: 2424-2426

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Expeditous Synthesis of Benzopyrans via Lewis Acid-Catalyzed C-H Functionalization: Remarkable Enhancement of Reactivity by an OrthoSubstituent2010

    • Author(s)
      Mori, K.; Kawasaki, T.; Sueoka. S.; Akiyama, T
    • Journal Title

      Org. Lett

      Volume: 12 Issue: 8 Pages: 1732-1735

    • DOI

      10.1021/ol100316k

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Expeditious Synthesis of Benzopyrans via Lewis Acid-Catalyzed C-H Functionalization : Remarkable Enhancement of Reactivity by an Ortho Substituent2010

    • Author(s)
      森啓二
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 1732-1735

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 分子内redox反応を利用した多環骨格の迅速構築2012

    • Author(s)
      森 啓二
    • Organizer
      第一回有機触媒若手セミナー
    • Place of Presentation
      ラフォーレ那須
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Concise Route to Isoquinoline Skeleton by Lewis Acid-Catalyzed C(sp3)-H Bond Functionalization2012

    • Author(s)
      森 啓二
    • Organizer
      Tateshina Conference (2012)
    • Place of Presentation
      蓼科フォーラム
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Selective Activation of Enantiotopic C(sp3)-Hydrogen by Means of Chiral Phosphoric Acid: Asymmetric Synthesis of Tetrahydroquinoline Derivatives2012

    • Author(s)
      森 啓二
    • Organizer
      第一回日米有機触媒シンポジウム
    • Place of Presentation
      ハワイプリンスホテルワイキキ
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] 環状リン酸ジエステルを触媒とするC-H結合官能基化を利用したキノリン類の不斉合成2011

    • Author(s)
      森 啓二、江原 謙介、栗原 一樹、秋山 隆彦
    • Organizer
      第38回有機典型元素化学討論会
    • Place of Presentation
      石川県立音楽堂
    • Related Report
      2012 Final Research Report
  • [Presentation] 分子内redox反応を利用した多環骨格構築法の開発2011

    • Author(s)
      森 啓二
    • Organizer
      若手研究者のためのセミナー(有機合成化学協会関東支部)
    • Place of Presentation
      東京農工大学小金井キャンパス
    • Related Report
      2012 Final Research Report
  • [Presentation] Chiral Phosphoric Acid-CatalyzedC(sp3)-H Bond Functionalization: Asymmetric Synthesis of Tetrahydroquinoline Derivatives2011

    • Author(s)
      森啓二、江原 謙介、栗原 一樹、秋山 隆彦
    • Organizer
      First International Symposium on Moleculer Activation
    • Place of Presentation
      兵庫県淡路夢舞台国際会議場
    • Related Report
      2012 Final Research Report
  • [Presentation] 水素転位を介するC-H結合官能基化を利用した多環骨格構築法の開発2011

    • Author(s)
      森 啓二、末岡 晶作、川崎 太郎、大島 芳崇、秋山 隆彦
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部芝キャンパス
    • Related Report
      2012 Final Research Report
  • [Presentation] 水素転位を介するC-H結合官能基化を利用した多環骨格構築法の開発2011

    • Author(s)
      森 啓二
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      慶應大学薬学部
    • Related Report
      2011 Annual Research Report
  • [Presentation] 分子内redox反応を利用した多環骨格構築法の開発2011

    • Author(s)
      森 啓二
    • Organizer
      有機合成化学協会若手研究者のためのセミナー
    • Place of Presentation
      東京農工大学小金井キャンパス
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] 水素転位を介するC-H結合官能基化を利用した触媒的ヘテロ環骨格構築法の開発2010

    • Author(s)
      森啓二
    • Organizer
      第3回有機触媒シンポジウム
    • Place of Presentation
      東北大学片平キャンパス(宮城県)
    • Year and Date
      2010-09-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] ベンゾチアゾリンを水素供与体として用いた不斉還元反応の開発2010

    • Author(s)
      森啓二
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大学(東京都)
    • Year and Date
      2010-05-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] Expeditious Synthesis of Quinazoline Derivatives via Bronsted Acid-Induced C-H Functionalization: Further Extension of "tert-Amino Effect"2010

    • Author(s)
      森啓二、大島 芳崇、江原 謙介、秋山 隆彦
    • Organizer
      2010 PACIFICHEM
    • Place of Presentation
      ハワイコンベンションセンター
    • Related Report
      2012 Final Research Report
  • [Presentation] 水素転位を介する C-H 結合官能基化を利用した触媒的ヘテロ環骨格構築法の開発2010

    • Author(s)
      森 啓二、江原 謙介、川崎 太郎、栗原 一樹、秋山 隆彦
    • Organizer
      第3回有機触媒シンポジウム
    • Place of Presentation
      東北大学青葉山キャンパス
    • Related Report
      2012 Final Research Report
  • [Book] 金属を使わずに水素を活性化できるのか?「月刊化学」"最新のトピックス"2011

    • Author(s)
      森 啓二、秋山 隆彦
    • Publisher
      化学同人
    • Related Report
      2012 Final Research Report
  • [Book] 化学2011

    • Author(s)
      森啓二
    • Publisher
      化学同人
    • Related Report
      2010 Annual Research Report
  • [Book] 「鉄触媒を用いたクロスカップリング反応の新展開」「有機合成化学協会誌」"Review de Dedut"2010

    • Author(s)
      森 啓二
    • Publisher
      有機合成化学協会
    • Related Report
      2012 Final Research Report
  • [Remarks]

    • URL

      http://www-cc.gakushuin.ac.jp/%7E940020/akiyama_site/

    • Related Report
      2012 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2016-04-21  

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