Development of novel chiral bronsted acid catalyst based on intramolecular hydrogen bonding

• Project/Area Number: 20550045
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Hiroshima University
• Principal Investigator: TAKAGI Ryukichi Hiroshima University, 大学院・理学研究科, 助教 (90304394)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 合成有機化学 / 有機分子触媒 / 不斉反応 / 水素結合 / Diels-Alder反応 / 不斉合成 / ブレンステッド酸

Research Abstract

A novel chiral bronsted acid catalyst based on intramolecular hydrogen bonding have been developed. The novel chiral bronsted acid slightly accelerated the Diels-Alder reaction of cross-conjugated dienone and cyclopentadiene than the original one. ONIOM calculations suggested that the chiral bronsted acid interact with the dienone by double hydrogen bond in the Diels-Alder reaction.

Research Products

• [Journal Article] Concentration and Temperature Dependency of Regio- and Stereoselectivity in a Photochemical [2+2] Cycloaddition Reaction (the Paterno-Buchi Reaction) : Origin of the Hydroxy-GroupDirectivity (2011)
  • Author(s): Yabuno, Youhei; Hiraga, Yoshikazu; Takagi, Ryukichi; Abe, Manabu.
  • Journal Title: J.Am. Chem. Soc. 133 Pages: 2592-2604
  • Peer Reviewed
• [Journal Article] Zirconium-catalyzed chemoselective methylalumination of ethers, amines, and sulfides bearing two terminal alkenyl groups (2011)
  • Author(s): Takagi, Ryukichi ; Igata, Nao ; Yamamoto, Kazuhiro ; Kojima, Satoshi
  • Journal Title: Journal of Organometallic Chemistry Volume: (掲載確定)
  • Peer Reviewed
• [Journal Article] Computational study on the cyclopropanation reaction of ylides generated from α-pyridiniumacetates. (2010)
  • Author(s): Matsumura, Shuji; Takagi, Ryukichi; Kojima, Satoshi; Ohkata, Katsuo; Abe, Manabu.
  • Journal Title: Heterocycles 81 Pages: 2479-2495
  • NAID: 40017340088
  • Peer Reviewed
• [Journal Article] Alkylalumination of arylacetylene catalyzed by zirconocene catalysts supported on solid materials. (2010)
  • Author(s): Takagi, Ryukichi; Igata, Nao; Yamamoto, Kazuhiro; Kojima, Satoshi.
  • Journal Title: Journal of Molecular Catalysis A : Chemical 321 Pages: 71-76
  • Peer Reviewed
• [Journal Article] Computational study on the cyclopropanation reaction of ylides generated from α-pyridiniumacetates (2010)
  • Author(s): Matsumura, Shuji ; Takagi, Ryukichi ; Kojima, Satoshi ; Ohkata, Katsuo ; Abe, Manabu
  • Journal Title: Heterocycles Volume: 81 Pages: 2479-2495
  • NAID: 40017340088
  • Peer Reviewed
• [Journal Article] Concentration and Temperature Dependency of Regio- and Stereoselectivity in a Photochemical [2+2] Cycloaddition Reaction (the Paterno -Buchi Reaction) : Origin of the Hydroxy-GroupDirectivity (2010)
  • Author(s): Yabuno, Youhei ; Hiraga, Yoshikazu ; Takagi, Ryukichi ; Abe, Manabu
  • Journal Title: Journal of the American Chemical Society Volume: 133 Pages: 2592-2604
  • Peer Reviewed
• [Journal Article] Alkylalumination of arylacetylene catalyzed by zirconocene catalysts supported on solid materials (2010)
  • Author(s): 高木隆吉
  • Journal Title: Journal of Molecular Catalysis A : Chemical (掲載決定)
  • Peer Reviewed
• [Journal Article] Construction of the Adamantane Core of Plukenetione-Type Polycyclic Polyprenylated Acylphloroglucinols. (2008)
  • Author(s): Takagi, Ryukichi; Inoue, Yuta; Ohkata, Katsuo.
  • Journal Title: J.Org. Chem. 73 Pages: 9320-9325
  • Peer Reviewed
• [Journal Article] Construction of the Adamantane Core of Plukenetione-Type Polycyclic Polyprenylated Acylphloroglucinols (2008)
  • Author(s): 高木隆吉
  • Journal Title: The Journal of Organic Chemistry 73 Pages: 9320-9325
  • Peer Reviewed
• [Journal Article] Zirconium-catalyzed chemoselective methylalumination of ethers, amines, and sulfides bearing two terminal alkenyl groups.
  • Author(s): Takagi, Ryukichi; Igata, Nao; Yamamoto, Kazuhiro; Kojima, Satoshi.
  • Journal Title: J.Organomet. Chem. accepted.
  • Peer Reviewed
• [Presentation] シクロペンタン-1,3-ビラジカルのスピン制御に基づくテトララジカルのスピン整列 (2011)
  • Author(s): 岡本一茂・高木隆吉・安倍学
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2011-03-27
• [Presentation] 一重項1,3-ビラジカルの寿命に及ぼす2位の置換基効果 (2010)
  • Author(s): 中垣知幸・坂井智子・藤原好恒・高木隆吉・安倍学
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-09
• [Presentation] 励起状態アゾ化合物の反応性に及ぼす置換基効果:β-炭素-炭素結合開裂の機構解明 (2010)
  • Author(s): 田村大志・高木隆吉・安倍学
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-09
• [Presentation] 低温マトリクス中におけるビラジカルの光反応 (2010)
  • Author(s): 前田倫・高木隆吉・安倍学
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-09
• [Presentation] グラブス試薬を用いた末端ジエン類の分子内[3+2]型環化付加反応 (2010)
  • Author(s): 山本幸明・高木隆吉・安倍学
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-26
• [Presentation] グラブス試薬を用いた末端ジエン類の分子内[3+2]型環化付加反応 (2010)
  • Author(s): 高木隆吉
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪府)
  • Year and Date: 2010-03-26
• [Presentation] ジルコノセン触媒を用いたメチルアルミニウム化反応におけるヘテロ原子の影響 (2009)
  • Author(s): 井形直央・山本和弘・高木隆吉・小島聡志・安倍学
  • Organizer: 第89日本化学会春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-29
• [Presentation] 閉環メタセシス反応を含むタンデム反応による環状化合物の合成研究 (2009)
  • Author(s): 山本幸明・田中賢治・高木隆吉・大方勝男・安倍学
  • Organizer: 第89日本化学会春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-28
• [Presentation] 連続的Michael反応を用いたPlukenetione Aの中心骨格合成と不斉合成の検討 (2008)
  • Author(s): 近藤広理・井上祐太・藤井絵美・高木隆吉・大方勝男
  • Organizer: 第50回天然有機化合物討論会
  • Place of Presentation: 福岡
  • Year and Date: 2008-10-01
• [Presentation] ジルコノセン触媒を用いたアルキルアルミニウム化反応における助触媒の効果 (2008)
  • Author(s): 井形直央・山本和弘・高木隆吉・小島聡志
  • Organizer: 第57回高分子討論会
  • Place of Presentation: 大阪
  • Year and Date: 2008-09-25