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2008 Fiscal Year Final Research Report

Development of Efficient Cascade Reactions with Unsaturated Carbonyl

Research Project

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Project/Area Number 17065014
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionKyoto University

Principal Investigator

TOMIOKA Kiyoshi  Kyoto University, 薬学研究科, 教授 (50114575)

Co-Investigator(Kenkyū-buntansha) KENICHI Yamada  京都大学, 薬学研究科, 准教授 (00335184)
YAMAMOTO Yasutomo  京都大学, 薬学研究科, 助教 (10452278)
Project Period (FY) 2005 – 2008
Keywords連続化反応 / 合成力量 / 環境調和 / 原子効率 / 有機合成
Research Abstract

廃棄物の低減および資源リサイクルは21世紀最重要課題の1つである。連続反応の開発は反応や精製過程で生じる廃棄物を低減できるので上記目的に貢献しうる。我々は不飽和カルボニル系が連続的に複数の化学結合形成が可能な官能基である点に着目し、有用化合物の構築反応の開発を行なった。その結果、彼岸花アルカロイド(-)-lycorine、海洋アルカロイド(+)-halichlorine、インドールアルカロイド(-)-aspidospermidineなど強力な生理活性を有する天然物をはじめとする有用化合物合成法の開発に成功した。

  • Research Products

    (45 results)

All 2009 2008 2007 2006 2005

All Journal Article (26 results) (of which Peer Reviewed: 26 results) Presentation (18 results) Book (1 results)

  • [Journal Article] Total Synthesis of (-)-Lycorine and (-)-2- epi-Lycorine by Asymmetric Conjugate Addition Cascade.2009

    • Author(s)
      Yamada, K.; Yamashita, M.; Sumiyoshi, T.; Nishimura, K.; Tomioka, K.
    • Journal Title

      Org. Lett. 11(7)

      Pages: 1631-1633

    • Peer Reviewed
  • [Journal Article] Aminolithiation of Carbon-Carbon Double Bonds as a Powerful Tool in Organic Synthesis.2009

    • Author(s)
      Tomioka, K.; Sakai, T.; Ogata, T.; Yamamoto Y.
    • Journal Title

      Pure Appl. Chem. 81(2)

      Pages: 247-253

    • Peer Reviewed
  • [Journal Article] Asymmetric Construction of Quaternary Carbon Centers by Sequential Conjugate Addition of Lithium Amide and in situ Alkylation: Utility in the Synthesis of (-)-Aspidospermidine.2009

    • Author(s)
      Suzuki, M.; Kawamoto, Y.; Sakai, T.; Yamamoto, Y.; Tomioka, K.
    • Journal Title

      Org. Lett. 11(3)

      Pages: 653-655

    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Asymmetric Allylic Substitution with Aryl and Ethyl Grignard Reagents.2008

    • Author(s)
      Selim, K.; Yamada, K.; Tomioka, K.
    • Journal Title

      Chem. Commun. (41)

      Pages: 5140-5142

    • Peer Reviewed
  • [Journal Article] Consecutive Cyclization of Allylaminoalkene by Intramolecular Aminolithiation-Carbolithiation.2008

    • Author(s)
      Tsuchida, S.; Kaneshige, A.; Ogata, T.; Baba, H.; Yamamoto, Y.; Tomioka, K.
    • Journal Title

      Org. Lett. 10(16)

      Pages: 3635-3638

    • Peer Reviewed
  • [Journal Article] Copper-catalyzed Asymmetric Alkylation of Imines with Dialkylzinc and Related Reactions.2008

    • Author(s)
      Yamada, K.; Tomioka, K.
    • Journal Title

      Chem. Rev. 108(8)

      Pages: 2874-2886

    • Peer Reviewed
  • [Journal Article] A Ternary Complex Reagent for an Asymmetric Michael Reaction of Lithium Ester Enolates with Enoates.2008

    • Author(s)
      Yamamoto, Y.; Suzuki, H.; Yasuda, Y.; Tomioka, K.
    • Journal Title

      Tetrahedron Lett. 49(31)

      Pages: 4582-4584

    • Peer Reviewed
  • [Journal Article] C_2 Symmetric Chiral NHC Ligand for Asymmetric Quaternary Carbon Constructing Copper-Catalyzed Conjugate Addition of Grignard Reagents to 3-Substituted Cyclohexenones.2008

    • Author(s)
      Matsumoto, Y.; Yamada, K.; Tomioka, K.
    • Journal Title

      J. Org. Chem. 73(12)

      Pages: 4578-4581

    • Peer Reviewed
  • [Journal Article] Base-Induced Sequential Cyclization-Rear-rangement of Enantioenriched 3-Aminoalkanoates to Five- and Seven-Membered Lactams.2008

    • Author(s)
      Sakai, T.; Yamada, K.; Tomioka, K.
    • Journal Title

      Chem. Asian J. 3(8)

      Pages: 1486-1493

    • Peer Reviewed
  • [Journal Article] Amidophosphane-Copper(I)-Catalyzed Asymmetric Conjugate Addition of Dialkylzinc Reagents to Racemic 6-Substituted Cyclohexenones to Form 2, 5-Di- and 2, 2, 5-Trisubstituted Cyclohexanone.2008

    • Author(s)
      Selim, K.; Soeta, T.; Yamada, K.; Tomioka, K.
    • Journal Title

      Chem. Asian J. 3(2)

      Pages: 342-350

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Intramolecular Hydroamination of Aminoalkenes.2007

    • Author(s)
      Ogata, T.; Ujihara, A.; Tsuchida, S.; Shimizu, T.; Kaneshige, A.; Tomioka, K.
    • Journal Title

      Tetrahedron Lett. 48(38)

      Pages: 6648-6650

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 3-Amino-2-hydroxyalkanoates by Mannich Reaction of Menthyl Acetate with Imines and Subsequent Oxidation.2007

    • Author(s)
      Hata, S.; Tomioka, K.
    • Journal Title

      Tetrahedron 63(35)

      Pages: 8514-8520

    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of 5-Substituted Cycloalkenones by Peptidic Amidophosphane-Copper-Catalyzed Asymmetric Conjugate Addition of Dialkylzinc.2007

    • Author(s)
      Soeta, T.; Selim, K.; Kuriyama, M.; Tomioka, K.
    • Journal Title

      Tetrahedron 63(28)

      Pages: 6573-6576

    • Peer Reviewed
  • [Journal Article] Peptidic Amidomonophosphane Ligand for Copper-Catalyzed Asymmetric Conjugate Addition of Diorganozincs to Cycloalkenones.2007

    • Author(s)
      Soeta, T.; Selim, K.; Kuriyama, M.; Tomioka, K.
    • Journal Title

      Adv. Synth. Catal. 349

      Pages: 629-635

    • Peer Reviewed
  • [Journal Article] Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides.2006

    • Author(s)
      Duguet, N.; Harrison-Marchand, A.; Maddaluno, J.; Tomioka, K.
    • Journal Title

      Org. Lett. 8(25)

      Pages: 5745-5748

    • Peer Reviewed
  • [Journal Article] Efficient Catalytic Asymmetric Synthesis of trans-2-substituted 5-Arylcyclohexanones by Rhodium-Catalyzed Conjugate Arylation of Racemic 6-Substituted Cyclohexenones.2006

    • Author(s)
      Chen, Q.; Soeta, T.; Kuriyama, M.; Yamada, K.; Tomioka, K.
    • Journal Title

      Adv. Synth. Catal. 348(18)

      Pages: 2604-2608

    • Peer Reviewed
  • [Journal Article] C_2 Symmetric Chiral N-Heterocyclic Carbene Catalyst for Asymmetric Intramolecular Stetter Reaction.2006

    • Author(s)
      Matsumoto, Y.; Tomioka, K.
    • Journal Title

      Tetrahedron Lett. 47(33)

      Pages: 5843-5846

    • Peer Reviewed
  • [Journal Article] Chiral Ligand-Controlled Asymmetric Conjugate Amination of Enoates with Lithium Mesitylmethyl(trimethylsilyl)amide.2006

    • Author(s)
      Sakai, T.; Doi, H.; Tomioka, K.
    • Journal Title

      Tetrahedron 62(35)

      Pages: 8351-8359

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Reactions Using Environmentally Friendly Reagents And Catalyst. Asymmetric Synthesis vs Kinetic Resolution.2006

    • Author(s)
      Tomioka, K.
    • Journal Title

      Pure Appl. Chem. 78(11)

      Pages: 2029-2034

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Intermediates for Otamixaban and Premafloxacin by the Chiral Ligand-Controlled Asymmetric Conjugate Addition of a Lithium Amide.2006

    • Author(s)
      Sakai, T.; Kawamoto, Y.; Tomioka, K.
    • Journal Title

      J. Org. Chem. 71(12)

      Pages: 4706-4709

    • Peer Reviewed
  • [Journal Article] Asymmetric Mannich-Type Addition of Lithium Glycolates to Imines Producing 3-Hydroxy-4-phenylazetidin-2-ones.2005

    • Author(s)
      Fujieda, H.; Hata, S.; Yamada, K.; Tomioka, K.
    • Journal Title

      Heterocycles 66

      Pages: 611-619

    • Peer Reviewed
  • [Journal Article] Chiral Amidophosphane-Copper Catalyzed Asymmetric Conjugate Addition of Dialkylzinc Reagents to Nitroalkenes.2005

    • Author(s)
      Valleix, F.; Nagai, K.; Soeta, T.; Kuriyama, M.; Yamada, K.; Tomioka, K.
    • Journal Title

      Tetrahedron 61(31)

      Pages: 7420-7424

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Addition of Terminal Alkynes to Aldehydes Mediated by (1R, 2R)-2-(Dimethylamino)-1, 2-diphenylethanol.2005

    • Author(s)
      Yamashita, M.; Yamada, K.; Tomioka, K.
    • Journal Title

      Adv. Synth. Catal. 347(11-13)

      Pages: 1649-1652

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of 5-Arylcyclohexenones by Rhodium(I)-Catalyzed Conjugate Arylation of Racemic 5-(Trimethylsilyl)-cyclohexenone with Arylboronic Acid.2005

    • Author(s)
      Chen, Q.; Kuriyama, M.; Soeta, T.; Hao, X.; Yamada, K.; Tomioka, K.
    • Journal Title

      Org. Lett. 7(20)

      Pages: 4439-4441

    • Peer Reviewed
  • [Journal Article] Chiral Amino Alcohol-Mediated Asymmetric Conjugate Addition of Arylalkynes to Nitroolefins.2005

    • Author(s)
      Yamashita, M.; Yamada, K.; Tomioka, K.
    • Journal Title

      Org. Lett. 7(12)

      Pages: 2369-2371

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α, β-un-saturated N-2,4,6-Triisopropylphenylsulfon-ylaldimines with use of N-Boc-L-Val-Con-nected Amidophosphane-Copper(I) Catalyst.2005

    • Author(s)
      Soeta, T.; Kuriyama. M.; Tomioka, K.
    • Journal Title

      J. Org. Chem. 70(1)

      Pages: 297-300

    • Peer Reviewed
  • [Presentation] カルベン配位子の設計と不斉触媒反応への展開2009

    • Author(s)
      富岡清
    • Organizer
      徳島大学薬学部講演会
    • Place of Presentation
      徳島
    • Year and Date
      2009-01-28
  • [Presentation] Hydroamination of Carbon-Carbon Double Bond.2008

    • Author(s)
      Tomioka, K.
    • Organizer
      AI & Joan Meyers Memorial Symposium
    • Place of Presentation
      Fort Collins, Colorado, USA
    • Year and Date
      20081024-20081025
  • [Presentation] Hydroamination of Carbon-Carbon Double Bond for Nitrogen-Containing Heterocycles.2008

    • Author(s)
      Tomioka, K.
    • Organizer
      ICOS-17
    • Place of Presentation
      Daejeon, Korea
    • Year and Date
      20080622-20080627
  • [Presentation] 炭素炭素二重結合のヒドロアミノ化反応2008

    • Author(s)
      富岡清
    • Organizer
      長崎大学薬学部講演会
    • Place of Presentation
      長崎
    • Year and Date
      2008-11-11
  • [Presentation] Hydroamination of Carbon-Carbon Double Bond.2008

    • Author(s)
      Tomioka, K.
    • Organizer
      North Dacota State University Seminar
    • Place of Presentation
      USA
    • Year and Date
      2008-10-22
  • [Presentation] Hydroamination of Carbon-Carbon Double Bond.2008

    • Author(s)
      Tomioka, K.
    • Organizer
      North Carolina State University Seminar
    • Place of Presentation
      USA
    • Year and Date
      2008-10-20
  • [Presentation] 二重結合のヒドロアミノ化反応を基軸とする含窒素複素環の合成2008

    • Author(s)
      富岡清
    • Organizer
      有機合成夏期セミナー「明日の有機合成化学」
    • Place of Presentation
      大阪科学技術センター, 大阪
    • Year and Date
      2008-09-25
  • [Presentation] Asymmetric Amination for the Synthesis of Heterocycles.2008

    • Author(s)
      Tomioka, K.
    • Organizer
      5th Eurasian Meeting on Heterocyclic Chemistry Kuwait
    • Year and Date
      2008-03-03
  • [Presentation] Asymmetric Reactions for Amines.2007

    • Author(s)
      Tomioka, K.
    • Organizer
      Journees de Chimie Organique 2007
    • Place of Presentation
      France
    • Year and Date
      2007-09-18
  • [Presentation] The Development of C2 Symmetric Chiral Carbene Catalyzed Asymmetric Intramolecular Stetter Reaction.2006

    • Author(s)
      Matsumoto, Y.; Tomioka, K.
    • Organizer
      The 3rd Seoul-Kyoto-Osaka Joint Symposium on Pharmaceutical Sciences for Young Scientists
    • Place of Presentation
      Korea
    • Year and Date
      2006-11-27
  • [Presentation] Synthetic Study toward (+)-Pancratistatin.2006

    • Author(s)
      Ishii, N.; Tomioka, K.
    • Organizer
      The 3rd Seoul-Kyoto- Osaka Joint Symposium on Pharmaceutical Sciences for Young Scientists
    • Place of Presentation
      Korea
    • Year and Date
      2006-11-27
  • [Presentation] Catalytic Intramolecular Asymmetric Amination for the Short Step Alkaloid Synthesis.2006

    • Author(s)
      Ogata, T.; Ujihara, A.; Tomioka, K.
    • Organizer
      ICOB-5 and ISCNP-25 IUPAC
    • Place of Presentation
      Kyoto
    • Year and Date
      2006-07-24
  • [Presentation] Catalytic asymmetric reactions using environmentally friendly reagents and catalysts.2006

    • Author(s)
      Tomioka, K.
    • Organizer
      IUPAC 2nd International Symposium on Green/Sustainable Chemistry
    • Place of Presentation
      Delhi, India
    • Year and Date
      2006-01-13
  • [Presentation] Amidophosphane Ligands for Catalytic Asymmetric Reaction of Organometallics.2005

    • Author(s)
      Tomioka, K.
    • Organizer
      PACIFI CHEM 2005
    • Place of Presentation
      Hawaii
    • Year and Date
      2005-12-17
  • [Presentation] Direct Generation of Carbon Radicals by Cleavage of C-H and Utility in C-C Bond Formation.2005

    • Author(s)
      Tomioka, K.
    • Organizer
      PACIFI CHEM 2005
    • Place of Presentation
      Hawaii
    • Year and Date
      2005-12-17
  • [Presentation] Development of Asymmetric Reaction for the Synthesis of Biologically Potent Compounds.2005

    • Author(s)
      Tomioka, K.
    • Organizer
      The 3rd Japan-Korea Young Scientists Meeting on Bioorganic and Natural Products Chemistry
    • Place of Presentation
      Hyogo
    • Year and Date
      2005-09-25
  • [Presentation] Catalytic Asymmetric Carbon-Carbon Bond Formation with Chiral Amidophosphanes.2005

    • Author(s)
      Tomioka, K.
    • Organizer
      National Chao-Tung University
    • Place of Presentation
      Taiwan
    • Year and Date
      2005-05-27
  • [Presentation] 分子の基本的性質を基盤とする不斉付加反応2005

    • Author(s)
      富岡清
    • Organizer
      富士通Cacheセミナー
    • Place of Presentation
      東京
    • Year and Date
      2005-04-26
  • [Book] Science of Synthesis(Cumulenes, Allenes, Synthesis by Substitution.)2007

    • Author(s)
      Ohno H.; Tomioka, K.
    • Total Pages
      71-174
    • Publisher
      Houben-Weyl

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Published: 2011-06-18   Modified: 2016-04-21  

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