Development of synthesis of chiral nitrogen-containing building blocks

• Project/Area Number: 21750048
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: UCHIDA Tatsuya Kyushu University, 大学院・理学研究院, 助教 (50380564)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
• Keywords: 不斉合成 / キラルビルディングブロック / 含窒素化合物 / アジド / 低環境負荷 / ルテニウム / アジリジン化 / ナイトレン移動反応 / (+)-PD 128907 / 空気酸化 / 直接C-Hアミノ化 / 不斉アジリジン化 / 環境適応型反応 / アジド化合物 / 不斉反応 / サレン錯体

Research Abstract

We found that Ru(CO)-salen complex is a potent efficient catalyst for the aziridination of vinyl ketones with N-(2-trimethylsilyl)ethanesulfonyl azide as a nitrene precursor. The reaction generated with almost enantiomerically pure aziridino ketones. Furthermore, we could demonstrate that enantioselective short step formal synthesis of (+)-PD 128907 which is a potent dopamine D3 receptor agonist.

Research Products

• [Journal Article] Photopromoted Ru-Catalyzed Asymmetric Aerobic Sulfide Oxidation and Epoxidation Using Water as a Proton Transfer Mediator. (2010)
  • Author(s): Tanaka, H., Nishikawa, H., Uchida, T., Katsuki, T.
  • Journal Title: J.Am.Chem.Soc. 132(34) Pages: 12034-12041
  • Peer Reviewed
• [Journal Article] Photopromoted Ru-Catalyzed Asymmetric Aerbic Sulfide Oxidation and Epoxidation Using Water as a Proton Transfer Mediatorπ (2010)
  • Author(s): H.Tanaka, H.Nishikawa, T.Uchida, T.Katsuki
  • Journal Title: Journal of the American Chemical Society Volume: 132 Pages: 12034-12041
  • Peer Reviewed
• [Journal Article] Ru(PPh3)(OH)-salen complex : a Designer Catalyst for Chemoselective Aerobic Oxidation of Primary Alcohols. (2009)
  • Author(s): Mizoguchi, H., Uchida, T., Katsuki, T.
  • Journal Title: Tetrahedron Lett. 50(26) Pages: 3432-3435
  • Peer Reviewed
• [Journal Article] Construction of a New Type of Chiral Bidentate NHC Ligands : Copper-Catalyzed Asymmetric Conjugate Alkylation (2009)
  • Author(s): 内田竜也、香月勗
  • Journal Title: Tetrahedron Letters 50 Pages: 4741-4743
  • Peer Reviewed
• [Journal Article] Ru (PPh_3) (OH)-salen complex : a Designer Catalyst for Chemoselective Aerobic Oxidation of Primary Alcohols. (2009)
  • Author(s): 溝口大昴、内田竜也、香月勗
  • Journal Title: Tetrahedron Letters 50 Pages: 3432-3435
  • Peer Reviewed
• [Journal Article] Photopromoted Construction of a New Type of Chiral Bidentate NHC Ligands : Copper-Catalyzed Asymmetric Conjugate Alkylation. (2006)
  • Author(s): Uchida, T., Katsuki, T.
  • Journal Title: Tetrahedron Lett. 50(33) Pages: 4741-4743
  • Peer Reviewed
• [Presentation] 新規ルテニウムサレン錯体の合成と光非照射下での酸素酸化:第二級アルコールの速度論的光学分割 (2011)
  • Author(s): 溝口大昂、内田竜也、香月勗
  • Organizer: 第91回日本化学会春季年会
  • Place of Presentation: 横浜市・神奈川大学
  • Year and Date: 2011-03-28
• [Presentation] 不斉アジリジン化を鍵反応とするドーパミンD3受容体アゴニスト(+)-PD128907の不斉形式全合成 (2011)
  • Author(s): 福永恭章、内田竜也、香月勗
  • Organizer: 第91回日本化学会春季年会
  • Place of Presentation: 横浜市・神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] ルテニウム(CO)サレン触媒を用いたビニルケトンの不斉アジリジン化:光学的に純粋なアジリジノケトンの合成 (2010)
  • Author(s): 福永恭章、内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪市・近畿大学
  • Year and Date: 2010-03-28
• [Presentation] ルテニウム-サレン錯体を触媒とする不斉酸素酸化:オレフィンのエポキシ化 (2010)
  • Author(s): 田中春菜、内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪市・近畿大学
  • Year and Date: 2010-03-28
• [Presentation] 新規光学活性二座NHC-銅錯体を用いた不斉共役付加反応 (2010)
  • Author(s): 内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪市・近畿大学
  • Year and Date: 2010-03-28
• [Presentation] 新規光学活性二座NHC-銅錯体を用いた不斉共役付加反応 (2010)
  • Author(s): 内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪(近畿大学)
  • Year and Date: 2010-03-28
• [Presentation] ルテニウム-サレン錯体を触媒とする不斉酸素酸化:オレフィンのエポキシ化 (2010)
  • Author(s): 田中春菜、内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪(近畿大学)
  • Year and Date: 2010-03-28
• [Presentation] ルテニウム(CO)サレン触媒を用いたビニルケトンの不斉アジリジン化:光学的に純粋なアジリジノケトンの合成 (2010)
  • Author(s): 福永恭章、内田竜也、香月勗
  • Organizer: 第90回日本化学会春季年会
  • Place of Presentation: 大阪(近畿大学)
  • Year and Date: 2010-03-28
• [Presentation] Cu-Catalyzed Asymmetric Conjugate Addition of Dialkylzinc to Acyclic Enones Using a New Type of Chiral Bidentate NHC Ligands (2009)
  • Author(s): Tatsuya Uchida, Tsutomu Katsuki
  • Organizer: IKCOC-11
  • Place of Presentation: 京都市・リーガロイヤルホテル
  • Year and Date: 2009-11-11
• [Presentation] Design of New Ru(PPh3)(OH)-salen complex : Chemoselective Aerobic Oxidation of Primary Alcohols (2009)
  • Author(s): Hirotaka Mizoguchi, Tatsuya Uchida, Kohichi Ishida, Tsutomu Katsuki
  • Organizer: IKCOC-11
  • Place of Presentation: 京都市・リーガロイヤルホテル
  • Year and Date: 2009-11-11
• [Presentation] Cu-Catalyzed Asymmetric Conjugate Addition of Dialkylzinc to Acyclic Enones Using a New Type of Chiral Bidentate NHC Ligands (2009)
  • Author(s): 内田竜也、香月勗
  • Organizer: IKCOC-11
  • Place of Presentation: 京都(リーガロイヤルホテル京都)
  • Year and Date: 2009-11-11
• [Presentation] Design of New Ru(PPh_3) (OH)-salen complex : Chemoselective Aerobic Oxidation of Primary Alcohols (2009)
  • Author(s): 溝口大昴、内田竜也、香月勗
  • Organizer: IKCOC-11
  • Place of Presentation: 京都(リーガロイヤルホテル京都)
  • Year and Date: 2009-11-11
• [Remarks] ホームページ等
  • URL: http://www.scc.kyushu-u.ac.jp/Yuhan/Katsuki_Lab/Publication_List.html