Catalytic and Enantioselective Construction of Cyclohexane-fused Heterocycles

• Project/Area Number: 22790007
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: HARADA Shinji 千葉大学, 大学院・薬学研究院, 助教 (10451759)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2012: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 不斉合成 / 合成化学 / 不斉触媒 / ヒドロカルバゾール / 多環性骨格構築 / 触媒的不斉反応 / Diels-Alder反応 / ツリウム / ランタノイド / ビスチオウレア型配位子 / カルバゾール / 伊藤-三枝酸化

Research Abstract

The cycloaddition between siloxyvinyl-indole and dienophile gave hydrocarbazoles in up to quant. and 93% ee by using a novel chiral Thulium(III) catalyst. Synthetic application of adducts to biologically active compounds was also performed. It is noteworthy that this reaction system could be extendable to other heteroaromatic compounds.

Research Products

• [Journal Article] Abnormal Ito-Saegusa Oxidation of TIPS Enol Ether Assisted by a Hydroxy Group on a Side Chain (2011)
  • Author(s): Shiharu Hiraoka, Shinji Harada, Atsushi Nishida
  • Journal Title: Tetrahedron Lett Volume: 52 Issue: 24 Pages: 3079-3082
  • DOI: 10.1016/j.tetlet.2011.03.119
  • Peer Reviewed
• [Journal Article] Abnormal Ito-Saegusa Oxidation of TIPS Enol Ether Assisted by a Hydroxy Group on a Side Chain (2011)
  • Author(s): Shiharu Hiraoka, Shinji Harada, Atsushi Nishida
  • Journal Title: Tetrahedron Letter Volume: 52(In press)
  • Peer Reviewed
• [Presentation] 触媒的不斉Diels-Alder反応による多置換ヒドロカルバゾール合成 (2013)
  • Author(s): 代表:西田篤司(発表者:森川貴裕)
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜
  • Year and Date: 2013-03-29
• [Presentation] 触媒的不斉Diels-Alder反応による多置換ヒドロカルバゾール合成 (2012)
  • Author(s): 代表:西田篤司(発表者:森川貴裕)
  • Organizer: 第63回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京理科大学
  • Year and Date: 2012-05-19
• [Presentation] 触媒的不斉Diels-Alder反応による多置換ヒドロカルバゾール合成 (2012)
  • Author(s): 代表:西田篤司(発表者:森川貴裕)
  • Organizer: 第29回有機合成化学セミナー
  • Place of Presentation: 静岡県コンベンションアーツセンター
• [Presentation] Catalytic and Enantioselective Synthesis of Hydrocarbazoles by Diels-Alder Reaction (2012)
  • Author(s): 代表:西田篤司(発表者:原田真至)
  • Organizer: 19th International Conference on Organic Synthesis
  • Place of Presentation: Melbourne Convention Center, Australia(発表者:原田真至)
• [Presentation] New Chiral Ytterbium Catalyst Based on Binaphthyldiamine Ligands for Asymmetric Diels-Alder Reaction (2012)
  • Author(s): 代表:西田篤司(発表者:西田篤 司)
  • Organizer: BIT's 3rd Annual World Congress of Catalytic Asymmetric Synthesis-2012
  • Place of Presentation: Beijing International Convention Center, China
• [Presentation] Catalytic and Enantioselective Synthesis of Hydrocarbazoles by Diels-Alder Reaction (2012)
  • Author(s): Shinji Harada, Takahiro Morikawa, Atsushi Nishida
  • Organizer: 19th International Conference on Organic Synthesis
  • Place of Presentation: Melbourne Convention Center, Melbourne, Australia
• [Presentation] Enantioselective Diels-Alder Reaction of Danishefsky Type Diene Catalyzed by Chiral Yb(III) Complex and Its Application to the Total Synthesis of (-)-Platyphyllide (2011)
  • Author(s): 代表:西田篤司(発表者:原田真至)
  • Organizer: 8th AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: 京王プラザ ホテル
  • Year and Date: 2011-11-30
• [Presentation] Enantioselective Diels-Alder Reaction of Danishefsky Type Diene Catalyzed by Chiral Yb(III) Complex and Its Application tothe Total Synthesis of (-)-Platyphyllide□ (2011)
  • Author(s): ○Harada, S.; Hiraoka, S.; Toudou, N.; Li, K.; Nishida, A.
  • Organizer: 8^<th> AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: 京王プラザホテル(新宿)
  • Year and Date: 2011-11-30
• [Presentation] 二段階Diels-Alder反応による多環性骨格の触媒的不斉構築法の開発 (2011)
  • Author(s): 代表:西田篤司(発表者:李可〓)
  • Organizer: 第55回日本薬学会関東支部大会
  • Place of Presentation: 東邦大学
  • Year and Date: 2011-10-08
• [Presentation] 二段階Diels-Alder反応による多環性骨格の触媒的不斉構築法の開発 (2011)
  • Author(s): ○Li, K.; 平岡紫陽; 原田真至; 西田篤司
  • Organizer: 第55回 日本薬学会 関東支部大会
  • Place of Presentation: 東邦大学薬学部(習志野)
  • Year and Date: 2011-10-08
• [Presentation] Highly Enantioselective Diels-Alder Reactions of Danishefsky's Dienes with Electron-Deficient Alkenes Catalyzed by Yb(III)-BINAMIDE Complex (2010)
  • Author(s): 代表:西田篤司(発表者:原田真至)
  • Organizer: The International Chemical Congress of Pacific Basin Societies 2010
  • Place of Presentation: Honolulu, U.S.A.
  • Year and Date: 2010-12-17
• [Presentation] Highly Enantioselective Diels-Alder Reactions of Danishefsky's Dienes with Electron-Deficient Alkenes Catalyzed by Yb(III)-BINAMIDE Complexes (2010)
  • Author(s): Atsushi Nishida, Shiharu Hiraoka, Nozomi Toudou, Shinji Harada
  • Organizer: The international Chemical Congress of Pacific Basin Societies 2010 (Pacifichem 2010)
  • Place of Presentation: Hilton Hawaiian Village
  • Year and Date: 2010-12-17
• [Presentation] Yb錯体を用いたDanishefsky dieneの触媒的不斉Diels-Alder反応の開発 (2010)
  • Author(s): 代表:西田篤司
  • Organizer: 有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京農工大学(発表者:東道のぞみ)
  • Year and Date: 2010-05-22
• [Presentation] 不斉Diels-Alder反応を用いるPlatyphyllideの触媒的不斉全合成 (2010)
  • Author(s): 代表:西田篤司(発表者:平岡紫陽)
  • Organizer: 第8回次世代シンポ
  • Place of Presentation: 日本薬学会長井記念ホール
  • Year and Date: 2010-05-14
• [Presentation] Asymmetric Diels-Alder Reaction of Danishefsky-Type Diene Catalyzed by Chiral Yb(III)-Complex and Its Application to the Total Synthesis of Platyphyllide (2010)
  • Author(s): 代表:西田篤司(発表者:平 岡紫陽)
  • Organizer: 0th Cutting-Edge Organic Chemistry Junior Workshop
  • Place of Presentation: 国立清華大学, Taiwan
• [Presentation] 触媒的不斉Diels-Alder反応による多置換ヒドロカルバゾール合成
  • Author(s): 森川貴裕、原田真至、西田篤司
  • Organizer: 第63回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 東京理科大学野田キャンパス
• [Presentation] 触媒的不斉Diels-Alder反応による多置換ヒドロカルバゾール合成
  • Author(s): 森川貴裕、原田真至、西田篤司
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: パシフィコ横浜
• [Book] 使える!有機合成反応241 (2010)
  • Author(s): 丸岡啓二, 他、化学同人
  • Publisher: 実践ガイド
• [Remarks]
  • URL: http://www.p.chiba-u.ac.jp/lab/gousei/index.html
• [Remarks] 触媒的不斉Diels－Alder反応の開発
  • URL: http://www.p.chiba-u.ac.jp/lab/gousei/cn21/catalyst.html
• [Remarks] 発表論文リスト
  • URL: http://www.p.chiba-u.ac.jp/lab/gousei/publication.html