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2012 Fiscal Year Final Research Report

Development of Carbon-Carbon Bond Formation Reaction via Formation of Chiral Ion Pair

Research Project

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Project/Area Number 23655083
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

BABA Akio  大阪大学, 大学院・工学研究科, 教授 (20144438)

Co-Investigator(Renkei-kenkyūsha) NISHIMOTO Yoshihiro   (30550115)
Project Period (FY) 2011 – 2012
Keywords有機合成化学
Research Abstract

The coupling reaction of alcohol-derivatives with enol acetates was accomplished. This reaction is accelerated by a catalytic amount of indium trihalide to afford various types of α-alkylated ketones and aldehydes. Alkyl ethers, alkyl acetates, and silyl ethers were applicable to this reaction system.

  • Research Products

    (31 results)

All 2013 2012 2011 Other

All Journal Article (17 results) Presentation (13 results) Remarks (1 results)

  • [Journal Article] InCl3/Me3SiCl-Catalyzed Direct Michael Addition of Enol Acetates to α,β-Unsaturated Ketones2012

    • Author(s)
      Onishi, Y.; Yoneda, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 5788-5791

    • DOI

      DOI:10.1021/ol302888k

  • [Journal Article] Gallium Tribromide Catalyzed Coupling Reaction of Alkenyl Ethers with Ketene Silyl Acetals2012

    • Author(s)
      Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 8073-8076

    • DOI

      DOI:10.1002/anie.201203778

  • [Journal Article] Low Energy Metal Ion Beam Production with a Modified Freeman-Type Ion Source for Development of Novel Catalysts2012

    • Author(s)
      Yoshimura, S.; Kiuchi, M.; Nishimoto, Y.; Yasuda, M.; Baba, A.; Hamaguchi, S
    • Journal Title

      e-J. Surf. Sci. Nanotech.

      Volume: 10 Pages: 139-144

    • DOI

      DOI:10.1380/ejssnt.2012.139

  • [Journal Article] Dependence of Catalytic Properties of Indium-implanted SiO2 Thin Films on The Energy and Dose of Incident Indium Ions2012

    • Author(s)
      Yoshimura, S.; Kiuchi, M.; Nishimoto, Y.; Yasuda, M.; Baba, A.; Hamaguchi, S
    • Journal Title

      Thin Solid Films

      Volume: 520 Pages: 4894-4897

    • DOI

      DOI:10.1016/j.tsf.2012.03.028

  • [Journal Article] Lithium Phenolates with A Hexagonal-prismatic Li6O6 Core Isolated via A Cage-shaped Tripodal Ligands System: Crystal Structures and Their Behavior in Solution2012

    • Author(s)
      Nakajima, H.; Yasuda, M.; Baba, A
    • Journal Title

      Dalton Trans

      Volume: 41 Pages: 6602-6606

    • DOI

      DOI:10.1039/C2DT30266G

  • [Journal Article] Regio- and Stereoselective Carbobismuthination of Alkynes2012

    • Author(s)
      Nishimoto, Y.; Takeuchi, M.; Yasuda, M.; Baba, A
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 51 Pages: 1051-1054

    • DOI

      DOI:10.1002/anie.201107127.

  • [Journal Article] Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to AldehydesInamoto2012

    • Author(s)
      Inamoto, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 1168-1171

    • DOI

      DOI:10.1021/ol3001443

  • [Journal Article] Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes2012

    • Author(s)
      Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A
    • Journal Title

      Org. Lett

      Volume: 14 Pages: 1846-1849

    • DOI

      DOI:10.1021/ol300450j

  • [Journal Article] InI3/Me3SiI-catalyzed Direct Alkylation of Enol Acetates Using Alkyl Acetates or Alkyl Ethers2011

    • Author(s)
      Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A.
    • Journal Title

      Chem. Lett.

      Volume: 40 Pages: 1223-1225

    • DOI

      DOI:10.1246/cl.2011.1223

  • [Journal Article] Direct Synthesis of Alkynylstannanes: ZnBr2 Catalyst for the Reaction of Tributyltin Methoxide and Terminal Alkynes2011

    • Author(s)
      Kiyokawa, K.; Tachikake, N.; Yasuda, M.; Baba, A.
    • Journal Title

      Angew. Chem., Int. Ed

      Volume: 50 Pages: 10393-10396

    • DOI

      DOI:10.1002/anie.201104208

  • [Journal Article] Stabilization of Excited State Using Through-Space Interaction between Independent π-Systems Mediated by a peri-Substituted Hydroxy Group in 1-Arylnaphthalenes: Unexpected Blue Emission of 1,3,5-Tris(peri-hydroxynaphthyl)benzene2011

    • Author(s)
      Nakajima, H.; Yasuda, M.; Shimizu, K.; Toyoshima, N,; Tsukahara, Y.; Kobayashi, T.; Nakamura, S.; Chiba, K.; Baba, A
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 84 Pages: 1118-1129

    • DOI

      DOI:10.1246/bcsj.20110139

  • [Journal Article] Carbogallation of Alkynes Using Gallium Tribromide and Silyl Ketene Acetals and Synthetic Application to Cross-Coupling with Aryl Iodides2011

    • Author(s)
      Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A.
    • Journal Title

      Chem. Eur. J.

      Volume: 17 Pages: 11135-11138

    • DOI

      DOI:10.1002/chem.201102255

  • [Journal Article] Indium Tribromide Catalyzed Cross-Claisen Condensation between Carboxylic Acids and Ketene Silyl Acetals Using Alkoxyhydrosilanes2011

    • Author(s)
      Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 50 Pages: 8623-8625

    • DOI

      DOI:10.1002/anie.201104140

  • [Journal Article] InCl3/Me3SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates2011

    • Author(s)
      Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2762-2765

  • [Journal Article] Substituted Butenylindium Generated by Transmetalation of Cyclopropylmethylstannane with Indium Iodide: Synthesis and Characterization of Monobutenylindium2011

    • Author(s)
      Kiyokawa, K.; Yasuda, M.; Baba, A
    • Journal Title

      Organometallics

      Volume: 30 Pages: 2039-2043

    • DOI

      DOI:10.1021/ol200875m

  • [Journal Article] Synthesis of Cyclopropane-Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds2011

    • Author(s)
      Kiyokawa, K.; Suzuki, I.; Yasuda, M.; Baba, A
    • Journal Title

      Eur. J. Org. Chem

      Pages: 2163-2171

    • DOI

      DOI:10.1002/ejoc.201001471

  • [Journal Article] Recognition of Aromatic Compounds by Pocket within a Cage-Shaped Borate Catalyst

    • Author(s)
      Nakajima, H.; Yasuda, M.; Takeda, R. Baba, A.
    • Journal Title

      Angew. Chem., Int. Ed.

      Pages: 3867-3870

    • DOI

      DOI:10.1002/anie.201200346

  • [Presentation] 塩化亜鉛触媒による末端アルキンを用いたアセタール類の直接アルキニル化反応2013

    • Author(s)
      鈴木 至・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-25
  • [Presentation] 臭化ガリウム触媒によるケテンシリルアセタールとアルケニルエーテル類とのカップリング反応2013

    • Author(s)
      西本 能弘・上田博紀・今岡 洋人・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-23
  • [Presentation] 光学活性アミノアリルスズ種の金属交換を利用したカルボニル化合物との立体選択的反応2013

    • Author(s)
      安田 誠・長野 佳尚・馬場 章夫;
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-23
  • [Presentation] ヨウ化インジウム触媒によるヒドロシランと有機ケイ素求核剤を用いたアミドの多置換アミンへの直接変換反応2013

    • Author(s)
      稲本 佳寛・加賀 悠太・西本 能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-22
  • [Presentation] インジウム触媒と有機ケイ素化合物を利用したカルボン酸から第二級アルコールへの変換反応2013

    • Author(s)
      稲本 佳寛・西本能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-22
  • [Presentation] ヨウ化インジウムを用いたアレニルエーテルとケテンシリルアセタールのカップリング反応2013

    • Author(s)
      西村 貴至・西本 能弘・安田 誠・馬場 章夫
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Year and Date
      2013-03-22
  • [Presentation] 臭化ビスマスとケテンシリルアセタールによるアルキンの位置および立体選択的カルボビスマス化2012

    • Author(s)
      西本 能弘・竹内翠・安田 誠・馬場 章夫
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2012-09-14
  • [Presentation] 亜鉛および金属アルコキシド触媒によるアルキンとアセタールの直接カップリング反応2012

    • Author(s)
      鈴木 至・安田 誠・馬場 章夫
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2012-09-14
  • [Presentation] カゴ型ホウ素錯体の多様な修飾によるルイス酸性制御2012

    • Author(s)
      安田 誠・中岡 弘一・中島 秀人・馬場 章夫
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2012-09-14
  • [Presentation] Cage-Shaped Borate Esters with Multiple Tuning Factors: Geometric and Substitutent Effects on their Lewis Acid Properties2011

    • Author(s)
      Yasuda, M.; Nakajima, H.; Nakaoka, K.; Baba, A.
    • Organizer
      The 6th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-6) and The 2nd New PhaseInternational Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-2)
    • Place of Presentation
      Hong Kong
    • Year and Date
      20111211-15
  • [Presentation]2011

    • Author(s)
      Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A.
    • Organizer
      The Seventh International Symposiumon Integrated Synthesis (ISIS-7)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      20111009-10
  • [Presentation] Alkylindium Species for Coupling Reaction with Organic Halides in a Radical Manner2011

    • Author(s)
      Yasuda M.; Kiyokawa K.; Baba A
    • Organizer
      The 5th Pacific Symposium on Radical Chemistry(PSRC-5)
    • Place of Presentation
      Shirahama, Japan
    • Year and Date
      20110925-28
  • [Presentation] Radical Allylation of Iodo Phosphonates Using Organostannanes or Organoindiums2011

    • Author(s)
      Suzuki I.; Kiyokawa K.; Yasuda M.; Baba A
    • Organizer
      The 5th Pacific Symposium on Radical Chemistry (PSRC-5)
    • Place of Presentation
      Shirahama, Japan
    • Year and Date
      20110925-28
  • [Remarks]

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~babaken/index.html

URL: 

Published: 2014-09-25  

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