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Development of construction of multi-chiral center by one reaction ising meso trick

Research Project

Project/Area Number 23350043
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKobe University

Principal Investigator

HAYASHI MASAHIKO  神戸大学, 理学(系)研究科(研究院), 教授 (60192704)

Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥19,760,000 (Direct Cost: ¥15,200,000、Indirect Cost: ¥4,560,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2011: ¥14,300,000 (Direct Cost: ¥11,000,000、Indirect Cost: ¥3,300,000)
Keywordsメソ化合物 / 光学活性シッフ塩基 / 光学活性トリオール / オキシピリン類 / オゾン酸化 / シッフ塩基配位子 / オキシリピン類 / 光学活性アミノジオール / 光学活性ジアミノオール / 不斉合成 / 光学活性触媒 / 不斉アリル位酸化 / 不斉中心炭素
Research Abstract

Treatment of 4,5-epoxycyclohex-1-ene with ter-butylperbenzoic acid in the presence of Cu (I)-chiral N,N-bidente complex gave the (3S,4S,5S)-3-benzoyloxy-4-epoxycyclohexa-1-en in 54% chemical yield and 84% ee. The ee of this compound could be increased up to 100% ee by recrystalization after derivatization to the corresponding p-nitrobenzoyl derivative.
ring opening of the product epoxide with H2O followed by ozonolysis afforded the acyclic chiral triol. this method is useful for the synthesis of natural product such as oxylipines.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (54 results)

All 2014 2013 2012 Other

All Journal Article (21 results) (of which Peer Reviewed: 11 results) Presentation (29 results) (of which Invited: 1 results) Book (1 results) Remarks (3 results)

  • [Journal Article] Asymmetric Synthesis of cisand trans-2-Aryl-6-methylpyrans from D-Glucose via Arylation and Inversion of Configuration at C2-Position"2014

    • Author(s)
      K. Michigami, A. Shimazaki, and M. Hayashi
    • Journal Title

      Eur J. Org. Chem

      Volume: 2014 Issue: 1 Pages: 244-253

    • DOI

      10.1002/ejoc.201301376

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cleavage of 4,6-O-benzylidene Acetal Using Sodium Hydrogen Sulfate Monohydrate2013

    • Author(s)
      K. Michigami, M. Terauchi, and M. Hayashi
    • Journal Title

      Synthesis

      Volume: 45 Issue: 11 Pages: 1519-1523

    • DOI

      10.1055/s-0033-1338469

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Journal Article] Enantioselective Alkylation of Aldehydes Using Dialkylzincs Catalyzed by Simple Chiral Diols Derived from Naturally Occurring Monosaccharides2013

    • Author(s)
      K. Michigami and M. Hayashi
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 21 Pages: 4221-4225

    • DOI

      10.1016/j.tet.2013.03.090

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Journal Article] Practical preparation of chiral keto-imine type ONO Schiff base ligands2013

    • Author(s)
      V. Dhayalan, R. Murakami, and M. Hayashi
    • Journal Title

      Tetrahedron Asymmetry

      Volume: 24 (9-10) Issue: 9-10 Pages: 543-547

    • DOI

      10.1016/j.tetasy.2013.03.017

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Journal Article] Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Chiral Schiff Bases2013

    • Author(s)
      V. Dhayalan, R. Murakami, and M. Hayashi
    • Journal Title

      Asian J. Chem

      Volume: 25 (13) Pages: 7505-7508

    • Related Report
      2013 Final Research Report
  • [Journal Article] Synthesis of Novel Nucleosides and Stereoselectivity of N-Glycosidation2013

    • Author(s)
      K. Michigami, S. Uchida, M. Adachi, and M. Hayashi
    • Journal Title

      Tetrahedron

      Volume: 69 (2) Issue: 2 Pages: 595-599

    • DOI

      10.1016/j.tet.2012.11.017

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Alkynylation of Trifluoromethyl Ketones Catalyzed by Chiral Schiff Bases2013

    • Author(s)
      V. Dhayalan, R. Murakami, M. Hayashi
    • Journal Title

      Asian J. Chem

      Volume: 25

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Imidazole and Imidazoline Derivatives as N-Donor for Nickel-catalyzed Kumada-Tamao-Corriu Coupling2012

    • Author(s)
      R. Iwamoto and M. Hayashi
    • Journal Title

      Heterocycles

      Volume: 86 Issue: 1 Pages: 713-718

    • DOI

      10.3987/com-12-s(n)23

    • Related Report
      2013 Final Research Report
  • [Journal Article] Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using novel N,N,P-Cu(II) complex2012

    • Author(s)
      Y. Ebisu, K. Kawamura, and M. Hayashi
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 23 Issue: 13 Pages: 959-964

    • DOI

      10.1016/j.tetasy.2012.06.010

    • Related Report
      2013 Final Research Report
  • [Journal Article] Synthesis of 2-Arylbenzothiazole Derivatives Based on Activated Carbon-O2 Oxidation Followed by Suzuki-Miyaura Coupling2012

    • Author(s)
      V. Dhayalan and M. Hayashi
    • Journal Title

      Synthesis

      Volume: 44 Issue: 14 Pages: 2209-2216

    • DOI

      10.1055/s-0031-1289772

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of Secondary Benzylic Alcohols to Ketones and Benzylic Oxygenation of Alkylarenes with2012

    • Author(s)
      S. Nishida
    • Journal Title

      Synl;ett

      Volume: 2012 Issue: 11 Pages: 1683-1685

    • DOI

      10.1055/s-0031-1290367

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple Preparation of β-Amino Alcohols Possessing tert-Butyl Group at the Carbon Attached with Hydroxy Group2012

    • Author(s)
      J. T. Zacharia,T. Tanaka, Y. Uesaka, and M. Hayashi
    • Journal Title

      Synthesis

      Volume: 44 Issue: 11 Pages: 1625-1629

    • DOI

      10.1055/s-0031-1291039

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] HF-Pyridine : A versatile promoter for mo oacylation/sulfonylation of phenolic diols and for direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates2012

    • Author(s)
      K. Michigami, K. Yoshimoto, and M. Hayashi
    • Journal Title

      Chem. Lett

      Volume: 41 Issue: 2 Pages: 138-139

    • DOI

      10.1246/cl.2012.138

    • NAID

      10030223017

    • Related Report
      2013 Final Research Report
  • [Journal Article] Facile synthesis of acacetin-7-O-β-D-galactopyranoside2012

    • Author(s)
      J. T. Zacharia and M. Hayashi
    • Journal Title

      Carbohydr. Res

      Volume: 348 Pages: 91-94

    • DOI

      10.1016/j.carres.2011.11.015

    • Related Report
      2013 Final Research Report
  • [Journal Article] O- and N-Glycosidation of D-glycals using Ferrier rearrangement under Mitsunobu reaction conditions. Application to N-nucleoside synthesis2012

    • Author(s)
      K. Michigami and M. Hayashi
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 4 Pages: 1092-1096

    • DOI

      10.1016/j.tet.2011.11.084

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
  • [Journal Article] Niand Cu-catalyzed coupling reactions using 2-(4,5-dihydro-1H-imidazo-2-yl)phenol as a versatile phosphine-free ligand2012

    • Author(s)
      S. Haneda, K. Sudo, and M. Hayashi
    • Journal Title

      Heterocycles

      Volume: 84 Issue: 1 Pages: 569-575

    • DOI

      10.3987/com-11-s(p)20

    • Related Report
      2013 Final Research Report
  • [Journal Article] Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using novel N,N,P-Cu(II) complex2012

    • Author(s)
      Y. Ebisu
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 23 Pages: 959-964

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis2012

    • Author(s)
      J. T. Zacharia
    • Journal Title

      Simple Preparation of β-Amino Alcohols Possessing tert-Butyl Group at the Carbon Attached with Hydroxy Group

      Volume: 44 Pages: 1625-1629

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] HF-Pyridine : A versatile promoter for monoacylation/sulfonylation of phenolic diols and for direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates2012

    • Author(s)
      K.Michigami, K.Yoshimoto, M.Hayashi
    • Journal Title

      Chem.Lett

      Volume: 41 Pages: 138-139

    • NAID

      10030223017

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of acacetin-7-O-β-D-galactopyranoside2012

    • Author(s)
      J.T.Zacharia, M.Hayashi
    • Journal Title

      Carbohydr.Res.

      Volume: 348 Pages: 91-94

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ni- and Cu-catalyzed coupling reactions using 2-(4,5-dihydro-1H-imidazo-2-yl)phenol as a versatile phosphine-free ligand2012

    • Author(s)
      S.Haneda, K.Sudo, M.Hayashi
    • Journal Title

      Heterocycles

      Volume: 84 Pages: 569-575

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] 触媒的不斉アリル位酸化反応2013

    • Author(s)
      菅智幸, 石井昌美, 岩永和也, 譚啓濤, 林昌彦
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸(神戸大学)
    • Year and Date
      2013-08-02
    • Related Report
      2013 Final Research Report
  • [Presentation] C-アリールグリコシド化反応と脱酸素化-立体反転反応を組み合わせた光学活性 2-アリール-6-メチルピラン類の合成2013

    • Author(s)
      嶋崎敦子, 道上恭佑, 林昌彦
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸(神戸大学)
    • Year and Date
      2013-08-02
    • Related Report
      2013 Final Research Report
  • [Presentation] 光学活性な2-アリール-6-メチルピラン類の合成(1)2013

    • Author(s)
      道上恭佑, 林昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀 (立命館大学)
    • Related Report
      2013 Final Research Report
  • [Presentation] 光学活性な2-アリール-6-メチルピラン類の合成(2)2013

    • Author(s)
      嶋崎敦子, 道上恭佑, 林昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀 (立命館大学)
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規なN,N-二座配位子-銅錯体を用いた触媒的不斉アリル位酸化反応2013

    • Author(s)
      石井昌美, 岩永和也, 譚啓濤, 林昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀 (立命館大学)
    • Related Report
      2013 Final Research Report
  • [Presentation] 触媒的不斉アリル位酸化反応2013

    • Author(s)
      菅智幸,石井昌美, 岩永和也,譚 啓濤,林 昌彦
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Related Report
      2013 Annual Research Report
  • [Presentation] C-アリールグリコシド化反応と脱酸素化-立体反転反応を組み合わせた光学活性 2-アリール-6-メチルピラン類の合成2013

    • Author(s)
      嶋崎敦子,道上恭佑,林 昌彦
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Related Report
      2013 Annual Research Report
  • [Presentation] 光学活性シッフ塩基配位子を用いた触媒的不斉合成反応2013

    • Author(s)
      林 昌彦
    • Organizer
      化学道場
    • Place of Presentation
      広島
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 光学活性な2-アリール-6-メチルピラン類の合成(1)2013

    • Author(s)
      林 昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 光学活性な2-アリール-6-メチルピラン類の合成(2)2013

    • Author(s)
      林 昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 新規なN,N-二座配位子-銅錯体を用いた触媒的不斉アリル位酸化反応2013

    • Author(s)
      林 昌彦
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 光延反応を応用した不飽和グリコシドの合成法の開発2012

    • Author(s)
      道上恭佑, 林昌彦
    • Organizer
      本化学会第92春季年会
    • Place of Presentation
      横浜(慶應義塾大学)
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] グリコシドおよびその誘導体の効率的合成法の開発2012

    • Author(s)
      足立美峰, 道上恭佑, 内田怜志, 林昌彦
    • Organizer
      本化学会第92春季年会
    • Place of Presentation
      横浜(慶應義塾大学)
    • Year and Date
      2012-03-28
    • Related Report
      2011 Annual Research Report
  • [Presentation] 銅-シッフ塩基配位子系を用いたエノン類へのジアルキル亜鉛による不斉1,4-付加反応2012

    • Author(s)
      蛭子靖弘, 川村健二郎, 林昌彦
    • Organizer
      本化学会第92春季年会
    • Place of Presentation
      横浜(慶應義塾大学)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Kharasch-Sosnovosky Reaction of Cyclic Olefins2012

    • Author(s)
      M. Ishii,K. Iwanaga,Q. Tan,M. Hayashi
    • Organizer
      13th Tetrahedron Symposium - Asia Edition
    • Place of Presentation
      Taipei,Taiwan
    • Related Report
      2013 Final Research Report
  • [Presentation] Enantioselective Allylic Oxidation Catalized by N,N-Bidentate Ligand-Cu Complexes2012

    • Author(s)
      M. Ishii,K. Iwanaga,Q. Tan,M. Hayashi
    • Organizer
      12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      Kyoto, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Kharasch-Sosnovosky Reaction2012

    • Author(s)
      M. Ishii,K. Iwanaga,Q. Tan,M. Hayashi
    • Organizer
      2nd International Symposium on Molecular Activation,Todaiji Culture Center
    • Place of Presentation
      Nara, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] 環状オレフィンの不斉アリル位酸化反応2012

    • Author(s)
      石井昌美, 岩永和也, 譚啓濤, 林昌彦
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Reactions Using Chiral Schiff Base - Copper Complexes2012

    • Author(s)
      M. Hayashi
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC)
    • Place of Presentation
      Siem Reap, Cambodia
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Reactions Using Chiral Schiff Base - Copper Complexes2012

    • Author(s)
      M. Hayashi
    • Organizer
      17th Malaysian Chemical Congress (17MCC) 2012
    • Place of Presentation
      Kuaka Lumpur , Malaysia
    • Related Report
      2013 Final Research Report
  • [Presentation] 光延反応を応用した不飽和グリコシドの合成2012

    • Author(s)
      道上恭佑, 林昌彦
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Final Research Report
  • [Presentation] 光学活性な2-アリール-6-メチルピラン類の合成2012

    • Author(s)
      嶋崎敦子, 道上恭佑, 林昌彦
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Final Research Report
  • [Presentation] 光延反応を応用したO-およびN-グリコシル化反応2012

    • Author(s)
      道上恭佑 ,林昌彦
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Allylic Oxidation Using Novel N,N-Bidentate Ligand-Cu Complexes2012

    • Author(s)
      石井昌美, 岩永和也, 譚啓濤, 林昌彦
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪 (大阪大学)
    • Related Report
      2013 Final Research Report
  • [Presentation] Catalytic Asymmetric Kharasch-Sosnovosky Reaction2012

    • Author(s)
      M. Ishii,K. Iwanaga,Q. Tan,M. Hayashi
    • Organizer
      The 6th Takeda Science Foundation Symoisium on PharmaScience
    • Place of Presentation
      Osaka,Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] 触媒的不斉アリル位酸化反応2012

    • Author(s)
      石井昌美, 岩永和也, 譚啓濤, 林昌彦
    • Organizer
      日本プロセス化学会2012 サマーシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2013 Final Research Report
  • [Presentation] 活性炭を促進剤として用いる種々の酸化反応2012

    • Author(s)
      林昌彦
    • Organizer
      新学術領域「分子活性化」第3回公開シンポジウム
    • Place of Presentation
      金沢
    • Related Report
      2013 Final Research Report
  • [Presentation] Asymmetric Kharash-Sosnovsky Reaction of Cyclic Olefins2012

    • Author(s)
      林 昌彦
    • Organizer
      13th Tetrahedron symposium-Asia Edition
    • Place of Presentation
      Taipei
    • Related Report
      2012 Annual Research Report
  • [Presentation] Enantioselective Allylic Oxidation Catalyzed by N,N-Bidentate Ligand Cu-Complexes2012

    • Author(s)
      林 昌彦
    • Organizer
      12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Annual Research Report
  • [Book] 活性炭ハンドブック2012

    • Author(s)
      林昌彦、川下由加
    • Total Pages
      537
    • Publisher
      丸善
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www2.kobe-u.ac.jp/~mhayashi/

    • Related Report
      2013 Final Research Report
  • [Remarks] 神戸大学 有機反応化学研究室

    • URL

      http://www2.kobe-u.ac.jp/~mhayashi/

    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www2.kobe-u.ac.jp/~mhayashi/

    • Related Report
      2011 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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