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2013 Fiscal Year Final Research Report

Allylic and propargylic substitutions using the picolinoxy leaving group and application to organic synthesis

Research Project

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Project/Area Number 23550119
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

KOBAYASHI Yuichi  東京工業大学, 生命理工学研究科, 教授 (90153650)

Project Period (FY) 2011 – 2013
Keywordsアリル化反応 / 銅試薬 / アセチレン銅試薬 / ピコリン酸アリルエステル / リン酸アリルエステル / 第4級炭素構築 / シクロバクチオール / ジャスモン酸
Research Abstract

Allylic substitution of secondary allylic picolinates with copper reagents were investigated to establish methods for: (1) construction of quaternary carbon center; (2) synthesis of anti inflammatory cyclobakuchiols; (3) synthesis of trans 2,6-disubstituted cyclohexanones; (4) introduction of acetylene on a cyclopentane ring; (5) Pd-catalyzed allylic substitution of 1,3-disubstituted secondary allylic esters with ketone enolates.

  • Research Products

    (26 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (13 results) Remarks (1 results)

  • [Journal Article] Allylic substitution of esters derived from 2-bromocyclohex-2-enol with aryl copper reagents and synthetic utilization of the derived anti SN_2 products2014

    • Author(s)
      Ikoma, A. ; Kobayashi, Y
    • Journal Title

      Synlett

      Volume: 25 Pages: 1150-1154

    • DOI

      10.1055/s-0033-1341065

    • Peer Reviewed
  • [Journal Article] Synthesis of trans-2, 6-disubstituted cyclohexanones through allylic substitution2014

    • Author(s)
      Kobayashi, Y. ; Feng, C. ; Ikoma, A. ; Ogawa, N. ; Hirotsu, T
    • Journal Title

      Org. Lett

      Volume: 16 Pages: 760-763

    • DOI

      10.1021/ol403472y

    • Peer Reviewed
  • [Journal Article] Synthesis of cyclobakuchiols A, B, and C using conformation-controlled stereoselective reactions2014

    • Author(s)
      Kawashima, H. ; Kaneko, Y. ; Sakai, M. ; Kobayashi, Y
    • Journal Title

      Chem. Eur. J

      Volume: 20 Pages: 272-278

    • DOI

      10.1002/chem.201303538

    • Peer Reviewed
  • [Journal Article] Installation of a chiral side chain to a 2-alkylidene-1-cycloalkan-1-ol unit by using allylic substitution2013

    • Author(s)
      Feng, C. ; Kobayashi, Y
    • Journal Title

      Eur. J. Org. Chem

      Pages: 6666-6676

    • DOI

      10.1002/ejoc.201300792

    • Peer Reviewed
  • [Journal Article] Reinvestigation of palladium-catalyzed allylation of the monoacetate of 4-cyclopentene-1, 3-diol and synthesis of the coronafacic acid ethyl ester2013

    • Author(s)
      Kinouchi, W. ; Kosaki, Y. ; Kobayashi, Y
    • Journal Title

      Tetrahedron Lett

      Volume: 54 Pages: 7017-7020

    • DOI

      10.1016/j.tetlet.2013.10.052

    • Peer Reviewed
  • [Journal Article] Construction of quaternary carbon centers by using substitution of γ, γ-disubstituted secondary allylic picolinates with alkylcopper reagent2013

    • Author(s)
      Feng, C. ; Kaneko, Y. ; Kobayashi, Y
    • Journal Title

      Tetrahedron Lett

      Volume: 54 Pages: 4629-4632

    • DOI

      10.1016/j.tetlet.2013.06.046

    • Peer Reviewed
  • [Journal Article] Allylic substitution for construction of a chiral quaternary carbon possessing an aryl group2013

    • Author(s)
      Feng, C. ; Kobayashi, Y
    • Journal Title

      J. Org. Chem

      Volume: 78 Pages: 3755-3766

    • DOI

      10.1021/jo400248y

    • Peer Reviewed
  • [Journal Article] Synthesis of the amino acid conjugates of epi-jasmonic acid2012

    • Author(s)
      Ogawa, N. ; Kobayashi, Y
    • Journal Title

      Amino Acids

      Volume: 42 Pages: 1955-1966

    • DOI

      10.1007/s00726-011-0925-z

    • Peer Reviewed
  • [Journal Article] Efficient synthesis of substituted quinolines through intramoluecular addition of aryl anion to carbonyl carbon2012

    • Author(s)
      Kobayashi, Y. ; Igarashi, J. ; Feng, C. ; Tojo, T
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Pages: 3742-3745

    • DOI

      10.1016/j.tetlet.2012.05.003

    • Peer Reviewed
  • [Journal Article] シクロペンタ-4-エン-1, 3-ジオールのモノエステルを活用したシクロペンタノイド合成法の開発と応用2011

    • Author(s)
      小林雄一
    • Journal Title

      有合化

      Volume: 69 Pages: 680-690

    • DOI

      10.5059/yukigoseikyokaishi.69.680

    • Peer Reviewed
  • [Journal Article] Synthesis of an advanced intermediate toward the hNK-1 antagonist with the cyclopentane core2011

    • Author(s)
      Nakata, K. ; Kiyotsuka, Y. ; Kitazume, T. ; Kobayashi, Y
    • Journal Title

      Synlett

      Pages: 2872-2874

    • DOI

      10.1055/s-0031-1289863

    • Peer Reviewed
  • [Journal Article] Allylic substitution on cyclopentene and -hexene rings with alkynylcopper reagents2011

    • Author(s)
      Q. Wang. ; Kobayashi, Y
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 6252-6255

    • DOI

      10.1055/s-0031-1290006

    • Peer Reviewed
  • [Presentation] 有機リチウム試薬由来の銅試薬を用いるアリル化反応による四級炭素の構築2014

    • Author(s)
      尾崎拓里, 小林雄一
    • Organizer
      日化第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      20140327-30
  • [Presentation] コンフォメーション制御による不斉四級炭素構築法を基盤とするCyclobakuchiol類の合成2013

    • Author(s)
      川島英久, 金子悠希, 酒井将宏, 小林雄一
    • Organizer
      第104回有機合成化学シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Year and Date
      20131103-07
  • [Presentation] Total synthesis of cyclobakuchiols by conformation-controlled allylic substitution and michael addition2013

    • Author(s)
      Kawashima, H. ; Sakai, M. ; Kaneko, Y. ; Kobayashi, Y
    • Organizer
      10th International Symposium on Carbanion Chemistry
    • Place of Presentation
      Kyoto, Japan (同志社大学)
    • Year and Date
      20130923-26
  • [Presentation] 立体配座制御型アリル化反応を用いるCyclobakuchiol 類の合成2013

    • Author(s)
      川島英久, 酒井将宏, 小林雄一
    • Organizer
      日化第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-25
  • [Presentation] S_N2' 型アリル化反応を用いたアナストレフィンの合成研究2013

    • Author(s)
      酒井将宏, 小川熟人, 小林雄一
    • Organizer
      日化第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-23
  • [Presentation] アリル化反応を用いた光学活性な四級炭素の構築2013

    • Author(s)
      馮超, 小林雄一
    • Organizer
      日化第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-23
  • [Presentation] Pd 触媒を用いたアリル化合物とケトンエノレートの位置および立体選択的反応2013

    • Author(s)
      木野内渉, 小林雄一
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-22
  • [Presentation] Stereocontrolled synthesis of epi-jasmonoids, quinine alkaloids, and related compounds2012

    • Author(s)
      Kobayashi, Y
    • Organizer
      BIT's 3rd Annual World Congress of Catal. Asymmet. Synth. ; Session 800, Toward Highly Optically Pure Chemical Materials
    • Place of Presentation
      Beijing International Convention Center, China
    • Year and Date
      20120512-14
  • [Presentation] S_N2' 型アリル化反応を用いたシクロバクチオールAの合成研究2012

    • Author(s)
      酒井将宏, 小林雄一
    • Organizer
      日化第92春季年会
    • Place of Presentation
      慶應大学
    • Year and Date
      2012-03-28
  • [Presentation] α 位選択的プロパギル置換反応を利用したHeliannuol Eの合成研究2012

    • Author(s)
      金子未咲, 小林雄一
    • Organizer
      日化第92春季年会
    • Place of Presentation
      慶應大学
    • Year and Date
      2012-03-28
  • [Presentation] 環状構造を含む基質に対するアリル化反応の位置並びに立体選択性2012

    • Author(s)
      馮超, 小林雄一
    • Organizer
      日化第92春季年会
    • Place of Presentation
      慶應大学
    • Year and Date
      2012-03-28
  • [Presentation] Pd 触媒を用いたシス-4-シクロペンテン-1, 3-ジオールモノアセテートとβ-ケトエステルの反応ならびにその応用2012

    • Author(s)
      木野内渉, 東條敏史, 小林雄一
    • Organizer
      日化第92春季年会
    • Place of Presentation
      慶應大学
    • Year and Date
      2012-03-27
  • [Presentation] ピコリン酸2-ブロモ-2-シクロへキセニルのS_N2'反応を利用したクルクジオールの合成研究2012

    • Author(s)
      生駒篤, 小林雄一
    • Organizer
      日化第92春季年会
    • Place of Presentation
      慶應大学
    • Year and Date
      2012-03-25
  • [Remarks]

    • URL

      http://www.kobayashi.bio.titech.ac.jp

URL: 

Published: 2015-07-16  

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