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2012 Fiscal Year Final Research Report

Development of Innovative Molecular Transformations Via Cationic Rhodacycles as Active Species

Research Project

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Project/Area Number 20675002
Research Category

Grant-in-Aid for Young Scientists (S)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

TANAKA Ken  東京農工大学, 大学院・工学研究院, 教授 (40359683)

Project Period (FY) 2008 – 2012
Keywords有機合成 / 触媒反応 / 不斉合成 / 付加環化反応 / 芳香族化合物
Research Abstract

In this research, the method of generating various highly reactive cationic rhodacycles was examined in detail , and many novel catalyses which involve these intermediates as active species were developed. These developed catalyses were expanded to the asymmetrical catalyses that are able to construct axial, planar, helical, and multiple central chiralities, and syntheses of functional organic materials. Thus, "chemistry of cationic rhodacycles " was established.

  • Research Products

    (43 results)

All 2013 2012 2011 2010 2009 2008 Other

All Journal Article (24 results) (of which Peer Reviewed: 24 results) Presentation (10 results) Book (3 results) Remarks (1 results) Patent(Industrial Property Rights) (5 results) (of which Overseas: 4 results)

  • [Journal Article] Enantioselective Synthesis of Planar Chiral Carba-Paracyclophanes: Rhodium-Catalyzed [2+2+2] Cycloaddition of Cyclic Diynes with Terminal Monoynes2013

    • Author(s)
      T. Araki, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 52 Pages: 5617-5621

    • DOI

      DOI:10.1002/anie.201300696

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Regio-, Diastereo-, and Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes with Acrylamides2012

    • Author(s)
      K. Masutomi, N. Sakiyama, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 13031-13035

    • DOI

      DOI:10.1002/anie.201206122

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Three-Component Cross-Addition of Silylacetylenes, Alkynyl Esters, and Electron-Deficient Alkenes or Isocyanates2012

    • Author(s)
      Y. Hoshino, Y. Shibata, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 9407-9411

    • DOI

      DOI:10.1002/anie.201204646

    • Peer Reviewed
  • [Journal Article] Rhodium- Catalyzed Cascade Reactions of Dienynes Leading to Substituted Dihydronaphthalenes and Naphthalenes2012

    • Author(s)
      E. Okazaki, R. Okamoto, Y. Shibata, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 6722-6727

    • DOI

      DOI:10.1002/anie.201202125

    • Peer Reviewed
  • [Journal Article] Dearomatization of Fused Arenes using Platinum-Catalyzed Intramolecular Double C-C Bond Formation2012

    • Author(s)
      T. Shibuya, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 6219-6222

    • DOI

      DOI:10.1002/anie.201202165

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Intramolecular Cyclization of Naphthol- or Phenol-Linked 1,6-Enynes via Cleavage and Formation of sp^2 C-O Bond2012

    • Author(s)
      N. Sakiyama, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 5976-5980

    • DOI

      DOI:10.1002/anie.201201186

    • Peer Reviewed
  • [Journal Article] Synthesis of Fluorene Derivatives through Rhodium-Catalyzed Dehydrogenative Cyclization, Angew2012

    • Author(s)
      K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura
    • Journal Title

      Chem. Int. Ed

      Volume: 51 Pages: 5359-5362

    • DOI

      DOI:10.1002/anie.201201526

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Enantioselective Synthesis, Crystal Structures, and Photophysical Properties of Helically Chiral 1, 1'-Bitriphenylenes2012

    • Author(s)
      Y. Sawada, S. Furumi, A. Takai, M. Takeuchi, K. Noguchi, K. Tanaka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 4080-4083

    • DOI

      DOI:10.1021/ja300278e

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Intermolecular [2+2+2] Cross-Trimerization of Aryl Ethynyl Ethers and Carbonyl Compounds To Produce Dienyl Esters2011

    • Author(s)
      Y. Miyauchi, M. Kobayashi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 10922-10926

    • DOI

      DOI:10.1002/anie.201105519

    • Peer Reviewed
  • [Journal Article] Catalytic [2+2+1] Cross-Cyclotrimerization of Silylacetylenes and Two Alkynyl Esters To Produce Substituted Silylfulvene2011

    • Author(s)
      Y. Shibata, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 10917-10921

    • DOI

      DOI:10.1002/anie.201105517

    • Peer Reviewed
  • [Journal Article] Rhodium- Catalyzed Highly Enantioselective Cyclizations of g-Alkynylaldehydes with Acyl Phosphonates: Ligand and Substituent-Controlled C-P or C-H Bond Cleavage2011

    • Author(s)
      K. Masuda, N. Sakiyama, R. Tanaka, K. Noguchi, K. Tanaka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 6918-6921

    • DOI

      DOI:10.1021/ja201337x

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Asymmetric Formal Olefination or Cycloaddition: 1,3-Dicarbonyl Compounds Reacting with 1,6-Diynes or 1,6-Enynes2011

    • Author(s)
      T. Suda, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 4475-4479

    • DOI

      DOI:10.1002/anie.201007727

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Enantioselective Intramolecular Hydroarylation of Alkynes To Form Axially Chiral 4-Aryl 2-quinolinones2011

    • Author(s)
      T. Shibuya, Y. Shibata, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 3963-3967

    • DOI

      DOI:10.1002/anie.201100152

    • Peer Reviewed
  • [Journal Article] Hierarchical Assembly of a Helicene Functionalized with Phthalhydrazide2011

    • Author(s)
      T. Kaseyama, S. Furumi, X. Zhang, K. Tanaka, M. Takeuchi
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 3684-3687

    • DOI

      DOI:10.1002/anie.201007849

    • Peer Reviewed
  • [Journal Article] Enantioselective Construction of Bridged Multicyclic Skeletons by Intermolecular [2 + 2 + 2] Cycloaddition/Intramolecular Diels- Alder Reaction Cascade2011

    • Author(s)
      M. Kobayashi, T. Suda, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 1664-1667

    • DOI

      DOI:10.1002/anie.201004150

    • Peer Reviewed
  • [Journal Article] Cationic Rhodium(I) Complex-Catalyzed [3 + 2] and [2 + 1] Cycloadditions of Propargyl Esters with Electron-Deficient Alkynes and Alkenes2010

    • Author(s)
      Y. Shibata, K. Noguchi, K. Tanaka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132 Pages: 7896-7898

    • DOI

      DOI:10.1021/ja102418h

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Asymmetric Reductive Cyclization of Heteroatom-Linked 5-Alkynals with Heteroatom-Substituted Acetaldehydes2010

    • Author(s)
      R. Tanaka, K. Noguchi, K. Tanaka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132 Pages: 1238-1239

    • DOI

      DOI:10.1021/ja9104655

    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral Tetrasubstituted Alkenes by an Asymmetric Cascade Reaction Catalyzed Cooperatively by Cationic Rhodium(I) and Silver(I) Complexes2009

    • Author(s)
      D. Hojo, K. Noguchi, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 48 Pages: 8129-8132

    • DOI

      DOI:10.1002/anie.200904024

    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Highly Enantioselective Direct Intermolecular Hydroacylation of 1,1-Disubstituted Alkenes with Unfunctionalized Aldehydes2009

    • Author(s)
      Y. Shibata, K. Tanaka
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 12552-12553

    • DOI

      DOI:10.1021/ja905908z

    • Peer Reviewed
  • [Journal Article] Cationic Rhodium (I)-dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade2009

    • Author(s)
      K. Tanaka, E. Okazaki, Y. Shibata
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 10822-10823

    • DOI

      DOI:10.1021/ja9038449

    • Peer Reviewed
  • [Journal Article] One-Step Construction of Five Successive Rings by Rh-Catalyzed Intermolecular Double [2+2+2] Cycloaddition: Enantioenriched [9] Helicene-Like Molecules2009

    • Author(s)
      K. Tanaka, N. Fukawa, T. Suda, K. Noguchi
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 48 Pages: 5470-5473

    • DOI

      DOI:10.1002/anie.200901962

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Spirocyclic Benzopyranones by Rhodium-Catalyzed Intermolecular [4 + 2] Annulation2008

    • Author(s)
      D. Hojo, K. Noguchi, M. Hirano, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 47 Pages: 5820-5822

    • DOI

      DOI:10.1002/anie.200801642

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of P-Stereogenic Alkynyl Phosphorus Compounds through Cationic Rh(I)/Modified-BINAP-Catalyzed [2 + 2 + 2] Cycloaddition2008

    • Author(s)
      G. Nishida, K. Noguchi, M. Hirano, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 47 Pages: 3410-3413

    • DOI

      DOI:10.1002/anie.200800144

    • Peer Reviewed
  • [Journal Article] Highly Regio-, Diastereo-, and Enantioselective [2 + 2 + 2] Cycloaddition of 1,6-Enynes with Electron-Deficient Ketones Catalyzed by a Cationic Rh(I)/H -binap Complex2008

    • Author(s)
      K. Tanaka, Y. Otake, H. Sagae, K. Noguchi, M. Hirano
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 47 Pages: 1312-1316

    • DOI

      DOI:10.1002/anie.200704758

    • Peer Reviewed
  • [Presentation] 芳香環構築反応の機能性物質合成への応用2012

    • Author(s)
      田中健
    • Organizer
      平成24年度(後期)有機合成化学講習会(招待講演)、日本薬学会長井記念ホール
    • Place of Presentation
      東京
    • Year and Date
      2012-11-21
  • [Presentation] Cationic Rhodium(I)/diene Complex-Catalyzed [2+2+1] and [2+2+2] Cross-Trimerization of Silylacetylenes and Unsaturated Compounds2012

    • Author(s)
      Ken Tanaka, Yu Shibata, Yuki Hoshino
    • Organizer
      17th Malaysian Chemical Congress 2012 (invited)
    • Place of Presentation
      Kuala Lumpur (Malaysia)
    • Year and Date
      2012-10-16
  • [Presentation] 芳香環構築によるキラル芳香族化合物の触媒的不斉合成2012

    • Author(s)
      田中健
    • Organizer
      第29回有機合成化学協会セミナー(Mukaiyama Award受賞講演)
    • Place of Presentation
      グランシップ静岡
    • Year and Date
      2012-09-06
  • [Presentation] アルキンの活性化を経由する新しい形式の触媒反応2011

    • Author(s)
      田中健
    • Organizer
      オルガノメタリックセミナー(招待講演)
    • Place of Presentation
      東京工業大学
    • Year and Date
      2011-11-18
  • [Presentation] Rhodium-Catalyzed Enantioselective Cyclizations of γ-Alkynylaldehydes with Acyl Phosphonates2011

    • Author(s)
      Ken Tanaka
    • Organizer
      OMCOS16
    • Place of Presentation
      Shanghai (China)
    • Year and Date
      2011-07-27
  • [Presentation] Enantioselective Construction of Helical Chirality by Rhodium-Catalyzed [2+2+2] Cycloaddition2011

    • Author(s)
      Ken Tanaka
    • Organizer
      3^<rd> UK/Japanese Conference in Catalytic Asymmetric Synthesis (invited)
    • Place of Presentation
      Oxford (UK)
    • Year and Date
      2011-04-14
  • [Presentation] Cationic Rhodium (I) Complexes for Asymmetric Catalysis2010

    • Author(s)
      Ken Tanaka
    • Organizer
      Pacifichem2010 (invited)
    • Place of Presentation
      Hawaii (USA)
    • Year and Date
      2010-12-15
  • [Presentation] Enantioselective Synthesis of Chiral Tetrasubstituted Alkenes Catalyzed Cooperatively by Cationic Rhodium (I) and Silver (I) Complexes2009

    • Author(s)
      Daiki Hojo, Ken Tanaka
    • Organizer
      IKCOC-11
    • Place of Presentation
      Kyoto
    • Year and Date
      2009-11-12
  • [Presentation] Cationic Rh (I) Complex-Catalyzed σ- and π -Bond Activation Cascade: Isomerization of Allyl Propargyl Ethers to Allenic Aldehydes and Dienals2009

    • Author(s)
      Ken Tanaka, Eri Okazaki, Yu Shibata
    • Organizer
      OMCOS15
    • Place of Presentation
      Glasgow (UK)
    • Year and Date
      2009-07-29
  • [Presentation] Enantioselective Synthesis of Chiral Ligands by Rhodium-Catalyzed [2 + 2 + 2] Cycloadditions (invited)2009

    • Author(s)
      Ken Tanaka
    • Organizer
      NCCJ 2009
    • Place of Presentation
      Tokyo
    • Year and Date
      2009-04-19
  • [Book] Synthesis of Helically Chiral Aromatic Compounds via [2+2+2] Cycloaddition2013

    • Author(s)
      K. Tanaka
    • Total Pages
      279-296
    • Publisher
      Transition-Metal-Mediated Aromatic Ring Construction; Tanaka, K. Ed.; Wiley: Hoboken
  • [Book] Rhodium-Mediated [2+2+2] Cycloaddition2013

    • Author(s)
      K. Tanaka
    • Total Pages
      127-160
    • Publisher
      Transition-Metal-Mediated Aromatic Ring Construction; Tanaka, K. Ed.; Wiley: Hoboken
  • [Book] C-H Bond Formation: Through Isomerization, Chemistry Molecular Sciences and Engineering2013

    • Author(s)
      K. Tanaka
    • Total Pages
      1-49
    • Publisher
      Reedijk, J. Ed.; Elsevier: Oxford
  • [Remarks]

    • URL

      http://www.tuat.ac.jp/~tanaka-k/Home.html

  • [Patent(Industrial Property Rights)] 軸不斉リン化合物とその製造方法2011

    • Inventor(s)
      田中健、横澤亨、袴田智彦
    • Industrial Property Rights Holder
      国立大学法人東京農工大学、高砂香料工業株式会社
    • Industrial Property Number
      特許、US13/041621
    • Filing Date
      2011-03-07
    • Overseas
  • [Patent(Industrial Property Rights)] 軸不斉イソキノリン誘導体及びその製造方法並びに不斉合成方法2010

    • Inventor(s)
      田中健
    • Industrial Property Rights Holder
      国立大学法人東京農工大学
    • Industrial Property Number
      特許、特願2010-173558
    • Filing Date
      2010-08-02
  • [Patent(Industrial Property Rights)] 軸不斉リン化合物とその製造方法2010

    • Inventor(s)
      田中健、横澤亨、袴田智彦
    • Industrial Property Rights Holder
      国立大学法人東京農工大学、高砂香料工業株式会社
    • Industrial Property Number
      特許、US8222433
    • Acquisition Date
      2010-03-23
    • Overseas
  • [Patent(Industrial Property Rights)] 軸不斉リン化合物とその製造方法2009

    • Inventor(s)
      田中健、西田剛士、横澤亨、遊佐雪徳
    • Industrial Property Rights Holder
      国立大学法人東京農工大学、高砂香料工業株式会社
    • Industrial Property Number
      特許、US12/396,751
    • Filing Date
      2009-03-03
    • Acquisition Date
      2012-07-17
    • Overseas
  • [Patent(Industrial Property Rights)] 新規光学活性ビアリールリン化合物とその製造方法

    • Inventor(s)
      田中健、栗山亙
    • Industrial Property Rights Holder
      国立大学法人東京農工大学、高砂香料工業株式会社
    • Industrial Property Number
      特許、US7683186
    • Overseas

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Published: 2014-08-29  

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