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2008 Fiscal Year Final Research Report

Development of Asymmetric Catalysis by Using Alkene

Research Project

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Project/Area Number 17065006
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionTokyo Institute of Technology

Principal Investigator

MIKAMI Koichi  Tokyo Institute of Technology, 大学院・理工学研究科, 教授 (10157448)

Co-Investigator(Renkei-kenkyūsha) AIKAWA Kohsuke  東京工業大学, 大学院・理工学研究科, 助教 (30401532)
Project Period (FY) 2005 – 2008
Keywords有機合成 / 不斉合成 / 原子効率 / エン反応 / カルボニル
Research Abstract

連続反応の緊密さは手法により異なるが、基質から反応中間体を単離することのないOne-pot反応はTandem (Domino)、中間体を単離しても化学変換することなく生成物を得られる連続反応はConsequtiveと定義される。いずれの連続反応も、中間体の官能基変換や保護・脱保護の必要な非連続反応とは対照的に、原子効率(Atom Economy)の良いGreenな反応となる。本研究ではプロセス有機合成化学の基礎となる「炭素資源の高度分子変換」を目的に、オレフィンの連続的な(不斉)分子変換反応を開発した。

  • Research Products

    (52 results)

All 2009 2008 2007 2006 2005 Other

All Journal Article (37 results) (of which Peer Reviewed: 37 results) Presentation (9 results) Book (4 results) Remarks (2 results)

  • [Journal Article] Dialkylzinc-accelerated α-Trifluoromethylation of Carbonyl Compounds Catalyzed by Late-transition-metal Complexes2008

    • Author(s)
      Tomita, Y.; Itoh, Y.; Mikami, K.
    • Journal Title

      Chem. Lett. 37(10)

      Pages: 1080-1081

    • Peer Reviewed
  • [Journal Article] Fluorous Substituent-based Enantiomer and Diastereomer Separation : Orthogonal Use of HPLC Columns for the Synthesis of Non-proteinogenic Polyfluoro Amino Acids and Peptides2008

    • Author(s)
      Tonoi, T.; Nishikawa, A.; Yajima, T.; Nagano, H.; Mikami, K.
    • Journal Title

      Eur. J. Org. Chem. (8)

      Pages: 1331-1335

    • Peer Reviewed
  • [Journal Article] Fluorous "Racemic" Mixture Synthesis : Chiral CHIRACEL Columns for Simultaneous Demix and Enantio-Separation of Racemic Fluorous-Tagged Compounds2008

    • Author(s)
      Tonoi, T.; Zhang, W.; Curran, D. P.; Mikami, K.
    • Journal Title

      Chirality 20(3-4)

      Pages: 597-603

    • Peer Reviewed
  • [Journal Article] Axial Chirality Control of Tropos BIPHEPs-Rh Complexes by Chiral Dienes : Synergy Effect in Catalytic Asymmetric Hydrogenation2008

    • Author(s)
      Aikawa, K.; Takabayashi, Y.; Kawauchi, S.; Mikami, K.
    • Journal Title

      Chem. Comm. (41)

      Pages: 5095-5097

    • Peer Reviewed
  • [Journal Article] Benzophenone-derived Catalysts with Self-adaptation : Highly Enantioselective Hydrogenation Irrespective of Substrates2008

    • Author(s)
      Wakabayashi, K.; Aikawa, K.; Mikami, K.
    • Journal Title

      Heterocycles 76(2)

      Pages: 1525-1535

    • Peer Reviewed
  • [Journal Article] Instant Chirality Control in Diphenylmethane-based Phosphoramidite Ligands : Highly Enantioselective Conjugate Addition to Nitroalkenes and Nitroacrylates2008

    • Author(s)
      Wakabayashi, K.; Aikawa, K.; Kawauchi, S.; Mikami, K.
    • Journal Title

      J. Am. Chem. Soc. 130(15)

      Pages: 5012-5013

    • Peer Reviewed
  • [Journal Article] Zincate-type enolate for radical α-trifluoromethylation2007

    • Author(s)
      Tomita, Y.; Ichikawa, Y.; Itoh, Y.; Kawada, K.; Mikami, K.
    • Journal Title

      Tetrahedron Lett. 48(50)

      Pages: 8922-8925

    • Peer Reviewed
  • [Journal Article] Enantiofacial Control of Planar Chiral Arene Ru Complexes Bearing Tropos Biphenyl Ligands2007

    • Author(s)
      Aikawa, K.; Kaito, I.; Mikami, K.
    • Journal Title

      Chem. Lett. 36(12)

      Pages: 1482-1483

    • Peer Reviewed
  • [Journal Article] Enantioselective Catalysis of Ketoester-Ene Reaction of Silyl Enol Ether to Construct Quaternary Carbons by Chiral Dicationic Palladium(II) Complexes2007

    • Author(s)
      Mikami, K.; Kawakami, Y.; Akiyama, K.; Aikawa, K.
    • Journal Title

      J. Am. Chem. Soc. 129(43)

      Pages: 12950-12951

    • Peer Reviewed
  • [Journal Article] Tandem Reductive Perfluoroalkylation of Esters with Perfluoroalkyl Titanate-Type Reagents2007

    • Author(s)
      Mikami, K.; Murase, T.; Itoh, Y.
    • Journal Title

      J. Am. Chem. Soc. 129(38)

      Pages: 11686-11687

    • Peer Reviewed
  • [Journal Article] Fluorous "Racemic" Mixture Synthesis : Simultaneous Strategy for Demixing and Enantioseparation of Racemic Fluorous-Tagged Products2007

    • Author(s)
      Tonoi, T.; Mikami, K.
    • Journal Title

      Eur. J. Org. Chem. (11)

      Pages: 1330-1333

    • Peer Reviewed
  • [Journal Article] Catalytic Asymmetric Synthesis and Anticancer Effects of the Novel Non-calcemic Analog of Vitamin D, 2α-Fluoro-19-nor-22-oxa-1α, 25-dihydroxyvitam in D3 in Metastatic Lung Carcinoma2007

    • Author(s)
      Nakagawa, K.; Okano, T.; Ozono, K.; Kato, S.; Kubodera, N.; Ohba, S.; Itoh, Y.; Mikami, K.
    • Journal Title

      J. Fluorine Chem. 128(6)

      Pages: 654-667

    • Peer Reviewed
  • [Journal Article] Dynamic Kinetic Resolution for the Catalytic Asymmetric Total Synthesis of Antithrombotic Agents M58163 and M581692007

    • Author(s)
      Saitoh, F.; Nishida, H.; Mukaihira, T.; Aikawa, K.; Mikami, K.
    • Journal Title

      Synth. Catal. 349(4-5)

      Pages: 617-628

    • Peer Reviewed
  • [Journal Article] Asymmetric Synergy between Chiral Dienes and Diphosphines in Cationic Rh(I)-Catalyzed Intramolecular [4+2] Cycloaddition2006

    • Author(s)
      Aikawa, K.; Akutagawa, S.; Mikami, K.
    • Journal Title

      J. Am. Chem. Soc. 128(39)

      Pages: 12648-12649

    • Peer Reviewed
  • [Journal Article] Experimental and Theoretical Studies on Radical Trifluoromethylation of Ti ate and Li Enolates2006

    • Author(s)
      Itoh, Y.; Houk, K. N.; Mikami, K.
    • Journal Title

      J. Org. Chem. 71(23)

      Pages: 8918-8925

    • Peer Reviewed
  • [Journal Article] Radical Trifluoromethylation of Ketone Li Enolates2006

    • Author(s)
      Itoh, Y.; Mikami, K.
    • Journal Title

      Tetrahedron Symposia-in-Print 62(30)

      Pages: 7199-7203

    • Peer Reviewed
  • [Journal Article] Chiral Aminoalcohol NOBIN for Instantaneous Chirality Control of Racemic but Tropos BIPHEP-Rh(I)-Complexes : Highly Enantioselective Ene-Type Cyclization of 1,6-Enynes Catalyzed by Rh(I)-Complexes without Use of Acid2006

    • Author(s)
      Mikami, K.; Kataoka, S.; Wakabayashi, K.; Aikawa, K.
    • Journal Title

      Tetrahedron Lett. 47(36)

      Pages: 6361-6364

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Antithrombotic Agents M58163 and M58169 : Dynamic Kinetic Resduction in Amide Formation Catalyzed by La-Linked BINOL Complex2006

    • Author(s)
      Saitoh, F.; Nishida, H.; Mukaihira, T.; Aikawa, K.; Mikami, K.
    • Journal Title

      Eur. J. Org. Chem. (24)

      Pages: 5454-5457

    • Peer Reviewed
  • [Journal Article] Radical Trifluoromethylation of Ketone Silyl Enol Ethers by Activation with Dialkylzinc2006

    • Author(s)
      Mikami, K.; Tomita, Y.; Ichikawa, Y.; Amikura, K.; Itoh, Y.
    • Journal Title

      Org. Lett. 8(21)

      Pages: 4671-4673

    • Peer Reviewed
  • [Journal Article] Modification of Alkoxo Ligands of BINOL-Ti Ladder : Isolation and X-ray Crystallographic Analysis2006

    • Author(s)
      Mikami, K.; Matsumoto, Y.; Xu, L.
    • Journal Title

      Inorganica Chimica Acta. 359(13)

      Pages: 4159-4167

    • Peer Reviewed
  • [Journal Article] Achiral Benzophenone Ligand-Rhodium Complex with Chiral Diamine Activator for High Enantiocontrol in Asymmetric Transfer Hydrogenation2006

    • Author(s)
      Mikami, K.; Wakabayashi, K.; Yusa, Y.; Aikawa, K.
    • Journal Title

      Chem. Comm. (22)

      Pages: 2365-2367

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Antithrombotic Agent M55529 : The First Enantioselective Cyclic N, O-Acetal Formation2006

    • Author(s)
      Saitoh, F.; Nishida, H.; Mukaihira, T.; Aikawa, K.; Mikami, K.
    • Journal Title

      Eur. J. Org. Chem. (10)

      Pages: 2269-2272

    • Peer Reviewed
  • [Journal Article] "Achiral" Benzophenone Ligand for Highly Enantioselective Ru-Catalysts in Ketone Hydrogenation2006

    • Author(s)
      Mikami, K.; Wakabayashi, K.; Aikawa, K.
    • Journal Title

      Org. Lett. 8(8)

      Pages: 1517-1519

    • Peer Reviewed
  • [Journal Article] A Useful Guideline for Rapid Separation and Identification of Fluorous Compounds by β-Cyclodextrin Columns2006

    • Author(s)
      Mikami, K.; Tonoi, T.; Matsuzawa, H.
    • Journal Title

      QSAR & Combinatorial Science 25(8-9)

      Pages: 766-768

    • Peer Reviewed
  • [Journal Article] Nanoflow Microreactor for Dramatic Increase not only in Reactivity but also in Selectivity: Baeyer-Villiger Oxidation by Aqueous Hydrogen Peroxide Using Lowest Concentration of a Fluorous Lanthanide Catalyst2006

    • Author(s)
      Mikami, K.; Yamanaka, M.; Islam, M. N.; Tonoi, T.; Itoh, Y.; Shinoda, M.; Kudo, K.
    • Journal Title

      J. Fluorine Chem., Special Issue for ACS Symposium 127(4-5)

      Pages: 592-596

    • Peer Reviewed
  • [Journal Article] Radical Trifluoromethylation of Ti Ate Enolate: Possible Intervention of Transformation of Ti(IV) to Ti(III) for Radical Termination2006

    • Author(s)
      Itoh, Y.; Mikami, K.
    • Journal Title

      J. Fluorine Chem., Special Issue for ACS Symposium 127(4-5)

      Pages: 539-544

    • Peer Reviewed
  • [Journal Article] Metal Enolates of α-CF3 Ketones : Theoretical Guideline, Direct Generation, and Synthetic Use2006

    • Author(s)
      Itoh, Y.; Mikami, K.
    • Journal Title

      Chemical Record 6(1)

      Pages: 1-11

    • Peer Reviewed
  • [Journal Article] Enantio-Discrimination and -Control of Neutral and Cationic Pt(II) Complexes Bearing Tropos BIPHEP Ligand : Its Application to Asymmetric Lewis Acid Catalysis2005

    • Author(s)
      Mikami, K.; Kakuno, H.; Aikawa, K.
    • Journal Title

      Angew. Chem. Int. Ed. 44(44)

      Pages: 7257-7260

    • Peer Reviewed
  • [Journal Article] Chiral Bis-trifluoromethanesulfonylamide as a Chiral Bronsted Acid Catalyst for the Asymmetric Hetero Diels-Alder Reaction with Danishefsky's Diene2005

    • Author(s)
      Tonoi, T.; Mikami, K.
    • Journal Title

      Tetrahedron Lett. 46(37)

      Pages: 6355-6358

    • Peer Reviewed
  • [Journal Article] Dual Chirality Control of Palladium(II) Complexes Bearing Tropos Biphenyl Diamine Ligands2005

    • Author(s)
      Aikawa, K.; Mikami, K.
    • Journal Title

      Chem. Commun. (46)

      Pages: 5799-5801

    • Peer Reviewed
  • [Journal Article] Tropos or Atropos Nature of Rh(I) Complexes Bearing a Tetrakis(phosphanyl)terphenyl (TETRAPHOS) Ligand : Highly Enantioselective Catalysis of Ene-type Cyclization2005

    • Author(s)
      Mikami, K.; Kataoka, S.; Aikawa, K.
    • Journal Title

      Org. Lett. 7(26)

      Pages: 5777-5780

    • Peer Reviewed
  • [Journal Article] Facile Radical Trifluoromethylation of Lithium Enolates2005

    • Author(s)
      Itoh, Y.; Mikami, K.
    • Journal Title

      Org. Lett. 7(22)

      Pages: 4883-4885

    • Peer Reviewed
  • [Journal Article] Theoretical Study on the Tropos Nature of the BIPHEP-Pd(II)/DABN and /DEPN Complexes: PIO Analysis of Phosphine-Pd(II) Interaction and Trans Influence2005

    • Author(s)
      Yamanaka, M.; Mikami, K.
    • Journal Title

      Organometallics 24(19)

      Pages: 4579-4587

    • Peer Reviewed
  • [Journal Article] Asymmetric Reduction of Ortho-multisubstituted Bwenzophenones Catalyzed by Diamine-Zn-Diol Complexes2005

    • Author(s)
      Ushio, H.; Mikami, K.
    • Journal Title

      Tetrahedron Lett. 46(16)

      Pages: 2903-2906

    • Peer Reviewed
  • [Journal Article] Enantioselective Heck-Type Reaction Catalyzed by tropos-Pd(II) Complex with Chiraphos Ligand2005

    • Author(s)
      Akiyama, K.; Wakabayashi, K.; Mikami, K.
    • Journal Title

      Adv. Synth. Catal 347(11-13)

      Pages: 1569-1575

    • Peer Reviewed
  • [Journal Article] Radical Trifluoromethylation of Titanium Ate Enolates2005

    • Author(s)
      Itoh, Y.; Mikami, K.
    • Journal Title

      Org. Lett. 7(4)

      Pages: 649-651

    • Peer Reviewed
  • [Journal Article] Chiral Aminonaphthol-catalyzed Enantioselective Carbonyl Addition of Diethylzinc to Aromatic Aldehydes High-Throughput Screened by CD-HPLC Analysis2005

    • Author(s)
      Xu, L.; Shen, X.; Zhang, C.; Mikami, K.
    • Journal Title

      Chirality 17(8)

      Pages: 476-480

    • Peer Reviewed
  • [Presentation] Asymmetric Catalytic Methods for Fluoroalkylation (招待講演)2009

    • Author(s)
      Mikami, K.
    • Organizer
      19th Winter Fluorine Conference
    • Place of Presentation
      Florida, U.S.A
    • Year and Date
      20090111-16
  • [Presentation] Tropos Catalysts for Industrial Processes of Catalytic Asymmetric Reactions (招待講演)2009

    • Author(s)
      Mikami, K.
    • Organizer
      1st Zach System Symposium 09
    • Place of Presentation
      Paris, France
    • Year and Date
      2009-05-15
  • [Presentation] Helical Chirality Control over Fluorous Tag and Substituent by Remote Center of Chirality (招待講演)2008

    • Author(s)
      Mikami, K.
    • Organizer
      International Meeting on Fluorinated-Peptide Chemistry
    • Place of Presentation
      Ochanomizu University, Tokyo, Japan
    • Year and Date
      2008-11-04
  • [Presentation] パイ電子系炭素分子の立体選択的分子変換(依頼講演)2007

    • Author(s)
      三上幸一
    • Organizer
      炭素資源の高度分子変換 第二回シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20070112-13
  • [Presentation] フッ素化学と遷移金属化学のNew Frontier(招待講演)2007

    • Author(s)
      三上幸一
    • Organizer
      有機合成化学協会東海支部 総合講演会
    • Place of Presentation
      三重
    • Year and Date
      2007-12-20
  • [Presentation] Two Decades After Yale with My Mentor (招待講演)2007

    • Author(s)
      Mikami, K.
    • Organizer
      Yale Symposium
    • Place of Presentation
      New Haven, U. S. A.
    • Year and Date
      2007-03-31
  • [Presentation] Enantio-Discrimination and -Control of Neutral and Cationic Metal Complexes Bearing Tropos Ligands : Application for Practical Asymmetric Synthesis (招待講演)2005

    • Author(s)
      三上幸一
    • Organizer
      味の素講演会
    • Place of Presentation
      川崎
    • Year and Date
      2005-12-01
  • [Presentation] Trifluoromethylation of Metal Enolates and Theoretical Guideline (招待講演)2005

    • Author(s)
      Mikami, K.
    • Organizer
      ACS Meeting Fluorine Symposium
    • Place of Presentation
      Washington D. C., U. S. A.
    • Year and Date
      2005-08-02
  • [Presentation] Fluorous Nanoflow Microreactor : Nanoflow Microreactor with Fluorous Lanthanide Catalysts for Increase in Reactivity and Selectivity (招待講演)2005

    • Author(s)
      Mikami, K.
    • Organizer
      ACS Meeting Fluorine Symposium
    • Place of Presentation
      Washington D. C., U. S. A.
    • Year and Date
      2005-08-02
  • [Book] Asymmetric Activation and Deactivation of Racemic Catalysts2007

    • Author(s)
      Mikami, K.; Aikawa, K.
    • Total Pages
      221-257
    • Publisher
      WILEY (In New Frontier in Asymmetric Catalsis; Mikami, K., Loutens, M., Eds. ; Chapter 8)
  • [Book] Chiral-Metal-Complex-Catalyzed Aliphatic Claisen Rearrangement2007

    • Author(s)
      Mikami, K.; Akiyama, K.
    • Total Pages
      25-43
    • Publisher
      WILEY-VCH (In The Claisen Rearrangemnet; Hiersemann, M., Nubbemeyer, U., Eds. ; Chapter 2)
  • [Book] Active Pd(II) Complexes as either Lewis Acid Catalysts or Transition Metal Catalysts2005

    • Author(s)
      Mikami, K.; Hatano, M.; Akiyama, K.
    • Total Pages
      279-321
    • Publisher
      Springer (In Topics in Organometallic Chemistry; Tsuji, J., Ed. ; 14 (Palladium in Organic Synthesis))
  • [Book] Ionic Liquids2005

    • Author(s)
      Jodry, J. J.; Mikami, K.
    • Total Pages
      1-58
    • Publisher
      Blackwell (In Green Reaction Media in Organic Synthesis; Mikami, K., Ed. ; Chapter 1-2)
  • [Remarks] 不斉合成で4級炭素構築医薬品産業などへ展開期待, 三上幸一, 科学新聞4面, 2007.9.28(新聞報道)

  • [Remarks] 独自触媒プロセス開発医薬中間体高品質・低コスト製造へ, 三上幸一, 日刊工業新聞24面, 2007.8.22(新聞報道)

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Published: 2010-06-10   Modified: 2016-04-21  

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