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

• Project/Area Number: 23655083
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Osaka 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
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: 有機合成化学 / 有機合成反応 / 触媒反応 / 有機化学

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

• [Journal Article] InCl_3/Me_3SiCl-Catalyzed Direct Michael Addition of Enol Acetates to α,β-Unsaturated Ketones (2012)
  • Author(s): 大西祥晴・米田勇樹・西本能弘・安田 誠・馬場章夫
  • Journal Title: Organic Letter Volume: 14 Issue: 22 Pages: 5788-5791
  • DOI: 10.1021/ol302888k
  • Peer Reviewed
• [Journal Article] Gallium Tribromide Catalyzed Coupling Reaction of Alkenyl Ethers with Ketene Silyl Acetals (2012)
  • Author(s): Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A
  • Journal Title: Angew. Chem. Int. Ed Volume: 51 Issue: 32 Pages: 8073-8076
  • DOI: 10.1002/anie.201203778
  • Peer Reviewed
• [Journal Article] Low Energy Metal Ion Beam Production with a Modified Freeman-Type Ion Source for Development of Novel Catalysts (2012)
  • Author(s): Yoshimura, S.; Kiuchi, M.; Nishimoto, Y.; Yasuda, M.; Baba, A.; Hamaguchi, S
  • Journal Title: e-Journal of Surface Science and Nanotechnology Volume: 10 Issue: 0 Pages: 139-144
  • DOI: 10.1380/ejssnt.2012.139
  • NAID: 130004438798
  • ISSN: 1348-0391
  • Peer Reviewed
• [Journal Article] Dependence of catalytic properties of indium-implanted SiO_2 thin films on the energy and dose of incident indium ions (2012)
  • Author(s): S. Yoshimura, M. Kiuchi, Y. Nishimoto, M. Yasuda, A. Baba, S. Hamaguchi
  • Journal Title: Thin Solid Films Volume: 520 Issue: 15 Pages: 4894-4897
  • DOI: 10.1016/j.tsf.2012.03.028
  • Peer Reviewed
• [Journal Article] Lithium Phenolates with A Hexagonal-prismatic Li6O6 Core Isolated via A Cage-shaped Tripodal Ligands System : Crystal Structures and Their Behavior in Solution (2012)
  • Author(s): 中島秀人、安田誠、馬場章夫
  • Journal Title: Dalton Trans. Volume: 41 Issue: 22 Pages: 6602-6606
  • DOI: 10.1039/c2dt30266g
  • Peer Reviewed
• [Journal Article] Regio- and Stereoselective Carbobismuthination of Alkynes (2012)
  • Author(s): 西本能弘
  • Journal Title: Angew.Chem.Int.Ed. Volume: 51 Issue: 4 Pages: 1051-1054
  • DOI: 10.1002/anie.201107127
  • Peer Reviewed
• [Journal Article] Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes (2012)
  • Author(s): Inamoto, Y.
  • Journal Title: Org. Lett. Volume: 14 Issue: 4 Pages: 1168-1171
  • DOI: 10.1021/ol3001443
  • Peer Reviewed
• [Journal Article] Recognition of Aromatic Compounds by II Pocket within a Cage-Shaped Borate Catalyst (2012)
  • Author(s): 中島秀人、安田誠、竹田陵祐、馬場章夫
  • Journal Title: Angew. Chem. Volume: 51 Issue: 16 Pages: 3867-3870
  • DOI: 10.1002/anie.201200346
  • Peer Reviewed
• [Journal Article] Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes (2012)
  • Author(s): Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A
  • Journal Title: Org. Lett Volume: 14 Issue: 7 Pages: 1846-1849
  • DOI: 10.1021/ol300450j
  • Peer Reviewed
• [Journal Article] InI3/Me3SiI-catalyzed Direct Alkylation of Enol Acetates Using Alkyl Acetates or Alkyl Ethers (2011)
  • Author(s): 大西祥晴・西本能弘・安田誠・馬場章夫
  • Journal Title: Chemistry Letters Volume: 40 Issue: 11 Pages: 1223-1225
  • DOI: 10.1246/cl.2011.1223
  • NAID: 130004426080
  • ISSN: 0366-7022, 1348-0715
  • Peer Reviewed
• [Journal Article] Direct Synthesis of Alkynylstannanes : ZnBr2 Catalyst for the Reaction of Tributyltin Methoxide and Terminal Alkynes (2011)
  • Author(s): Kensuke Kiyokawa, Nodoka Tachikake, Makoto Yasuda, Akio Baba
  • Journal Title: Angewandte Chemie International Edition Volume: Vol.50 Issue: 44 Pages: 10393-10396
  • DOI: 10.1002/anie.201104208
  • Peer Reviewed
• [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)benzene (2011)
  • Author(s): 中島秀人
  • Journal Title: Bull.Chem.Soc.Jpn. Volume: 84 Issue: 10 Pages: 1118-1129
  • DOI: 10.1246/bcsj.20110139
  • NAID: 130004152819
  • Peer Reviewed
• [Journal Article] Carbogallation of Alkynes Using Gallium Tribromide and Silyl Ketene Acetals and Synthetic Application to Cross-Coupling with Aryl Iodides (2011)
  • Author(s): Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A.
  • Journal Title: Chem. Eur. J. Volume: 17 Issue: 40 Pages: 11135-11138
  • DOI: 10.1002/chem.201102255
• [Journal Article] Indium Tribromide Catalyzed Cross-Claisen Condensation between Carboxylic Acids and Ketene Silyl Acetals Using Alkoxyhydrosilanes (2011)
  • Author(s): 西木能弘
  • Journal Title: Angew.Chem.Int.Ed. Volume: 50 Issue: 37 Pages: 8623-8625
  • DOI: 10.1002/anie.201104140
  • Peer Reviewed
• [Journal Article] InCl3/Me3SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates (2011)
  • Author(s): Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A.
  • Journal Title: Org. Lett Volume: 13 Pages: 2762-2765
• [Journal Article] InCl_3/Me_3SiBr-Catalyzed Direct Coupling between Silyl Ethers and Enol Acetates (2011)
  • Author(s): 大西祥晴・西本能弘・安田誠・馬場章夫
  • Journal Title: Organic Letters Volume: 13 Issue: 10 Pages: 2762-2765
  • DOI: 10.1021/ol200875m
  • Peer Reviewed
• [Journal Article] Synthesis of Cyclopropane-Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds (2011)
  • Author(s): Kiyokawa, K.; Suzuki, I.; Yasuda, M.; Baba, A
  • Journal Title: Eur. J. Org. Chem Volume: 2011 Issue: 11 Pages: 2163-2171
  • DOI: 10.1002/ejoc.201001471
• [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] 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): 加賀 悠太
  • 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
• [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
  • 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
• [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
  • 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
• [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
  • 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
• [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): 長野 佳尚
  • 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
• [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
  • 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
• [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 Properties (2011)
  • 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
• [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
• [Presentation] Alkylindium Species for Coupling Reaction with Organic Halides in a Radical Manner (2011)
  • Author(s): Yasuda M.; Kiyokawa K.; Baba A
  • Organizer: The 5th Pacific Symposium on Radical Chemistry(PSRC-5)
  • Place of Presentation: Shirahama, Japan
• [Presentation] Radical Allylation of Iodo Phosphonates Using Organostannanes or Organoindiums (2011)
  • 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
• [Presentation] Direct Coupling between Enol Acetates and Alkyl Acetates or Alkyl Ethers Catalyzed by Combined Lewis Acid of InI3 and Me3SiI (2011)
  • Author(s): Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A.
  • Organizer: The Seventh International Symposiumon Integrated Synthesis (ISIS-7)
  • Place of Presentation: シーサイドホテル舞子ビラ神戸（兵庫県）
• [Presentation] Selective Synthesis of b-Hydroxy- and b-Alkoxycarbonyl Compounds by Direct Transformation of Esters (2011)
  • Author(s): Yoshihiro Inamoto, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
  • Organizer: 58th Symposium on Organometallic Chemistry, Japan
  • Place of Presentation: 名古屋大学（愛知県）
• [Presentation] Indium Tribromide Catalyzed Radical Coupling of Internal Alkene-type Allyltins (2011)
  • Author(s): Itaru Suzuki, Kensuke Kiyokawa, Makoto Yasuda, Akio Baba
  • Organizer: 58th Symposium on Organometallic Chemistry, Japan
  • Place of Presentation: 名古屋大学（愛知県）
• [Remarks]
  • URL: http://www.chem.eng.osaka-u.ac.jp/~babaken/index.html