Development and Application of Selective Transformations for Diols by Multimetallic Catalysts

• Project/Area Number: 22790013
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Nagasaki University
• Principal Investigator: KURIYAMA Masami 長崎大学, 大学院・医歯薬学総合研究科, 准教授 (40411087)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2011: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 合成化学 / ジオール / 化学変換 / 触媒反応 / 遷移金属 / 銅 / パラジウム / スズ / アリール化 / アリル化 / 複合機能 / バイメタリック / 銅触媒 / カルベン / ハイブリッド型配位子

Research Abstract

The development of selective transformations for diols was conducted. Aryl and allyl groups were successfully introduced to diols by catalytic methods. In these reactions, high chemoselectivity and regioselectivity were achieved in addition to broad scope of substrates. The appropriate select of characteristics in metal catalyses realized high efficiency in these catalytic transformations.

Research Products

• [Journal Article] Synthesis of Optically Active Oxazoline Derivatives via Catalytic Asymmetric Desymmetrization of 1, 3-Diols (2012)
  • Author(s): Tsuda, Y.; Kuriyama, M.; Onomura, O.
  • Journal Title: Chem. Eur. J. Volume: 18 Pages: 2481-2483
  • Peer Reviewed
• [Journal Article] Monoallylation of 1, 2-Diols by Pd/ Sn Bimetallic Catalysis (2012)
  • Author(s): Kuriyama, M.; Takeichi, T.; Ito, M.; Yamasaki, N.; Yamamura, R.; Demizu, Y.; Onomura, O.
  • Journal Title: Chem. Eur. J. Volume: 18 Pages: 2477-2480
  • Peer Reviewed
• [Journal Article] Copper(II)-Catalyzed Monoarylation of Vicinal Diols with Diaryliodonium Salts (2012)
  • Author(s): Kuriyama, M.; Hamaguchi, N.; Onomura, O.
  • Journal Title: Chem. Eur. J. Volume: 18 Pages: 1591-1594
  • Peer Reviewed
• [Journal Article] Synthesis of Optically Active Oxazoline Derivatives via Catalytic Asymmetric Desymmetrization of 1,3-Diols (2012)
  • Author(s): Tsuda, Y.; Kuriyama, M.; Onomura, O.
  • Journal Title: Chem.Eur.J. Volume: 18 Issue: 9 Pages: 2481-2483
  • DOI: 10.1002/chem.201103800
  • Peer Reviewed
• [Journal Article] Monoallylation of 1,2-Diols by Pd/Sn Bimetallic Catalysis (2012)
  • Author(s): Kuriyama, M.; Takeichi, T.; Ito, M.; Yamasaki, N.; Yamamura, R.; Demizu, Y.; Onomura, O.
  • Journal Title: Chem.Eur.J. Volume: 18 Issue: 9 Pages: 2477-2480
  • DOI: 10.1002/chem.201102709
  • Peer Reviewed
• [Journal Article] Copper(II)-Catalyzed Monoarylation of Vicinal Diols with Diaryliodonium Salts (2012)
  • Author(s): Kuriyama, M.; Hamaguchi, N.; Onomura, O.
  • Journal Title: Chem.Eur.J. Volume: 18 Issue: 6 Pages: 1591-1594
  • DOI: 10.1002/chem.201102770
  • Peer Reviewed
• [Journal Article] Catalytic monosilylation of 1, 2-diols (2011)
  • Author(s): Takeichi, T.; Kuriyama, M.; Onomura, O.
  • Journal Title: Tetrahedron Lett. Volume: 52 Pages: 6646-6648
  • NAID: 120006985211
  • Peer Reviewed
• [Journal Article] Catalytic monosilylation of 1,2-diols (2011)
  • Author(s): Takeichi, T.; Kuriyama, M.; Onomura, O.
  • Journal Title: Tetrahedron Lett. Volume: 52 Issue: 49 Pages: 6646-6648
  • DOI: 10.1016/j.tetlet.2011.10.016
  • NAID: 120006985211
  • Peer Reviewed
• [Journal Article] Facile synthesis of optically active oxindols by copper-catalyzed asymmetric monotosylation of prochiral 1, 3-diols (2010)
  • Author(s): Kuriyama, M.; Tanigawa, S.; Kubo, Y.; Demizu, Y.; Onomura, O.
  • Journal Title: Tetrahedron : Asymmetry Volume: 21 Pages: 1370-1373
  • NAID: 120006984560
  • Peer Reviewed
• [Journal Article] Palladium-Imidazolinium Carbene-Catalyzed Arylation of Aldehydes with Arylboronic Acids in Water (2010)
  • Author(s): Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Onomura, O.
  • Journal Title: Tetrahedron Volume: 66 Pages: 6814-6819
  • NAID: 120006984284
  • Peer Reviewed
• [Journal Article] Facile synthesis of optically active oxindols by copper-catalyzed asymmetric monotosylation of prochiral 1,3-diols (2010)
  • Author(s): Kuriyama, M.; Tanigawa, S.; Kubo, Y.; Demizu, Y.; Onomura, O.
  • Journal Title: Tetrahedron : Asymmetry Volume: 21 Pages: 1370-1373
  • NAID: 120006984560
  • Peer Reviewed
• [Presentation] 準安定型配位を基盤とする配位子開発と触媒反応への適用 (2012)
  • Author(s): 栗山正巳
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学
  • Year and Date: 2012-03-29
• [Presentation] 準安定型配位を基盤とする配位子開発と触媒反応への適用 (2012)
  • Author(s): 栗山正巳
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 札幌
• [Presentation] 準安定二座型配位子を用いた効率的アリール化反応の開発 (2011)
  • Author(s): 栗山正巳
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: 静岡
• [Presentation] Palladium-Imidazolinium Carbene-Catalyzed Arylation of Aldehydes with Arylboronic Acids in Water (2010)
  • Author(s): Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Onomura, O.
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Hawaii
  • Year and Date: 2010-12-18
• [Presentation] Palladium-Imidazolinium Carbene-Catalyzed Arylation of Alde-hydes with Arylboronic Acids in Water (2010)
  • Author(s): Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Onomura, O.
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Hawaii, USA
• [Presentation] C-S二座型配位子-パラジウム錯体を用いたアルデヒドのジアステレオ選択的不斉アリール化反応 (2010)
  • Author(s): 栗山正巳
  • Organizer: 第1回有機分子構築法夏の勉強会
  • Place of Presentation: 蔵王
• [Patent(Industrial Property Rights)] 光学活性化合物又はその塩の製造方法 (2011)
  • Inventor(s): 尾野村治,津田悠太朗,栗山正巳,柳俊治,児玉和也
  • Industrial Property Rights Holder: 長崎大学,ナガセケムテックス株式会社
  • Filing Date: 2011-07-12
• [Patent(Industrial Property Rights)] 新規化合物とその錯体並びに錯体の製造方法 (2011)
  • Inventor(s): 尾野村治,栗山正巳,松尾星来,高瀬一郎
  • Industrial Property Rights Holder: 長崎大学,ダイセル化学工業株式会社
  • Filing Date: 2011-03-31
• [Patent(Industrial Property Rights)] 光学活性化合物又はその塩の製造方法 (2011)
  • Inventor(s): 尾野村治, 津田悠太朗, 栗山正巳, 柳俊治, 児玉和也
  • Industrial Property Rights Holder: 長崎大学,ナガセケムテックス株式会社
  • Industrial Property Number: 2011-153692
  • Filing Date: 2011-07-12
• [Patent(Industrial Property Rights)] ジオールのモノアリール化体の製造方法 (2010)
  • Inventor(s): 尾野村治,栗山正巳,山崎則次,伊藤雅章
  • Industrial Property Rights Holder: 長崎大学,ダイセル化学工業株式会社
  • Filing Date: 2010-04-23
• [Patent(Industrial Property Rights)] ジオールのモノアリール化体の製造方法 (2010)
  • Inventor(s): 尾野村治, 栗山正巳, 山崎則次, 伊藤雅章
  • Industrial Property Rights Holder: 長崎大学,ダイセル化学工業株式会社
  • Industrial Property Number: 2010-099631
  • Filing Date: 2010-04-23