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Development of direct allylation of amine catalyzed by Lewis acid

Research Project

Project/Area Number 22790023
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

KAWAI Nobuyuki  京都薬科大学, 薬学部, 助教 (10411034)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords合成化学 / ルイス酸 / 薬学 / 有機化学 / 触媒
Research Abstract

We have investigated the synthesis chiral non-racemic 1-alkenyl substituted tetrahydroisoquinoline 2 by the Bi(OTf)_3 catalyzed intramolecular cyclization of chiral non-racemic amino alcohol 1. The investigation of substituent effect on the benzene ring of 1 for the cyclization is described. Although 6-methoxy-1-propenyltetrahydroisoquinoline was obtained as a racemate, the corresponding 6-pivaloyloxytetrahydroisoquinoline was obtained stereospecifically in a 93 : 7 ratio. Based on the results, the synthesis of enantiopure 7-methoxy-6-pivaloyloxy-1-propenyltetrahydro isoquinoline has been accomplished, which converted to natural alkaloids, (+)-trolline and(-)-crispine A.

Report

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

    (19 results)

All 2012 2011 2010 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (11 results) Remarks (2 results)

  • [Journal Article] Determination of the absolute structure of (+)-akaterpin2012

    • Author(s)
      H. Hosoi, N. Kawai, H. Hagiwara, T. Suzuki, A. Nakazaki, K. Takao, K. Umezawa, S. Kobayashi
    • Journal Title

      Chem. Pharm. Bull

      Volume: Vol.60, No.1 Pages: 137-143

    • NAID

      130001852337

    • URL

      https://www.jstage.jst.go.jp/article/cpb/60/1/60_1_137/_pdf

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and determination of the relative structure of akaterpin, a potent inhibitor of PI-PLC2011

    • Author(s)
      H. Hosoi, N. Kawai, H. Hagiwara, T. Suzuki, A. Nakazaki, K. Takao, K. Umezawa, S.Kobayashi
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Issue: 38 Pages: 4961-4964

    • DOI

      10.1016/j.tetlet.2011.07.079

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of tetrahydroiso-quinoline alkaloids :(-)-trolline,(+)-crispin A,(+)-oleracein E2011

    • Author(s)
      N. Kawai, M. Matsuda, J. Uenishi
    • Journal Title

      Tetrahedron

      Volume: Vol.67, No.45 Issue: 45 Pages: 8648-8653

    • DOI

      10.1016/j.tet.2011.09.033

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pd^<II>-catalyzed cascade reaction with 1,3-chirality transfer ; stereoselective synthesis of chiral nonracemic 2,2'-THF-THF ring units2011

    • Author(s)
      Jun'ichi Uenishi, Yuhei Fujikura, Nobuyuki Kawai
    • Journal Title

      Org.Lett.

      Volume: 13 Issue: 9 Pages: 2350-2353

    • DOI

      10.1021/ol2005984

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of chiral 1-substituted tetrahydroisoquinolines by the intramolecular 1, 3-chirality transfer reaction catalyzed by Bi(OTf)_32011

    • Author(s)
      N. Kawai, M. Matsuda, J. Uenishi
    • Journal Title

      J. Org. Chem

      Volume: Vol.76, No.7 Issue: 7 Pages: 2102-2114

    • DOI

      10.1021/jo102452d

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral 1-Substituted Tetrahydroisoquinolines by the Intramolecular 1,3-Chirality Transfer Reaction Catalyzed by Bi(OTf)_32011

    • Author(s)
      Nobuyuki Kawai
    • Journal Title

      Journal of Organic Chemistry

      Volume: 76 Pages: 2102-2114

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Syhtesis of chiral 1-substituted tetrahydroisoquinoline by cyclization with neutral organocatalyst2011

    • Author(s)
      Nobuyuki Kawai, Koichi Ishibashi, Jun'ichi Uenishi
    • Organizer
      第2回プロセス化学国際シンポジウム
    • Place of Presentation
      京都国際会館(京都)
    • Year and Date
      2011-08-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] Neutral organocatalysts promoting dehydrative cyclization with 1, 3-chiralty transfer2011

    • Author(s)
      Nobuyuki Kawai
    • Organizer
      AIMECS11 8th AFMC International Medicinal Chemistry Symposium
    • Place of Presentation
      東京
    • Related Report
      2011 Final Research Report
  • [Presentation] スルホン酸エステルを触媒とする1, 3-不斉転写反応とテトラヒドロイソキノリンアルカイドの合成2011

    • Author(s)
      河井伸之
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2011 Final Research Report
  • [Presentation] 分子内1, 3-不斉転写反応を誘起する有機スルホン酸エステル触媒2011

    • Author(s)
      河井伸之
    • Organizer
      第61回日本薬学会近畿支部大会
    • Place of Presentation
      大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of chiral 1-substituted tetrahydroisoquinoline by cyclization with neutral organocatalyst2011

    • Author(s)
      Nobuyuki Kawai
    • Organizer
      第2回プロセス化学国際シンポジウム
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] スルホン酸エステル類を有機触媒とする環化反応のメカニズム2011

    • Author(s)
      河井伸之
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Related Report
      2011 Final Research Report
  • [Presentation] 6,7-位に酸素官能基を有する光学活性テトラヒドロイソキノリン環形成と関連するアルカロイドの不斉合成2010

    • Author(s)
      河井伸之
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台(日本)
    • Year and Date
      2010-10-16
    • Related Report
      2010 Annual Research Report
  • [Presentation] 光学活性1位置換テトラヒドロイソキノリン類の新規合成2010

    • Author(s)
      河井伸之
    • Organizer
      第60回日本薬学会近畿支部大会
    • Place of Presentation
      大阪
    • Related Report
      2011 Final Research Report
  • [Presentation] 光学活性テトラヒドロイソキノリン類の合成2010

    • Author(s)
      河井伸之
    • Organizer
      第37回有機反応懇談会
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] Catalytic intramolecular 1, 3-chirality transfer reaction to form azaheterocycles2010

    • Author(s)
      Nobuyuki Kawai
    • Organizer
      The 21st French-Japanese Symposium on Medicinal and Fine Chemistry
    • Place of Presentation
      京都
    • Related Report
      2011 Final Research Report
  • [Presentation] Bi(OTf)_3を触媒とする光学活性テトラヒドロイソキノリン誘導体の合成2010

    • Author(s)
      河井伸之
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.kyoto-phu.ac.jp/labo/yakka/

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.kyoto-phu.ac.jp/labo/yakka/

    • Related Report
      2011 Annual Research Report

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

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