Development of Outer-Sphere Control for Metal-Catalyzed Reactions

• Project/Area Number: 21750108
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Waseda University
• Principal Investigator: ENDO Kouhei Waseda University, 高等研究所, 助教 (70454064)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 有機合成 / 分子触媒 / 金属 / 外圏制御 / 反応有機化学 / 合成有機化学 / 選択的合成・反応 / 有機金属触媒 / 不斉合成 / 触媒設計・反応

Research Abstract

We achieved the efficient outer-sphere control of catalytic performance based on (1) the orbital interaction for diborylalkane, and (2) design of multinuclear catalyst for asymmetric reactions. The present studies demonstrated the novel strategy of neighboring effect that could not be established with the previous systems in organic chemistry.

Research Products

• [Journal Article] Multinuclear Pd/Zn Complex-Catalyzed Asymmetric Alkylative Ring-Opening Reaction of Oxabicyclic Alkenes (2011)
  • Author(s): Endo, K., Tanaka, K., Ogawa, M., Shibata, T.
  • Journal Title: Org.Lett. 13 Pages: 868-871
  • Peer Reviewed
• [Journal Article] Multinuclear Pd/Zn Complex-Catalyzed Asymmetric Alkylative Ring-Opening Reaction of Oxabicyclic Alkenes (2011)
  • Author(s): Kohei Endo, Keisuke Tanaka, Mika Ogawa, Takanori Shibata
  • Journal Title: Organic Letters Volume: 13 Pages: 868-871
  • Peer Reviewed
• [Journal Article] Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp^3-Carbon in 1,1-Diborylalkanes at Room Temperature (2010)
  • Author(s): Endo, K., Ohkubo, T., Hirokami, M., Shibata, T.
  • Journal Title: J.Am.Chem.Soc. 132 Pages: 11033-11035
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of Tetrasubstituted Alkenylboronates via 1,1-Organodiboronates (2010)
  • Author(s): Endo, K., Hirokami, M., Shibata, T.
  • Journal Title: J.Org.Chem. 75highlighted by Synfacts
  • Peer Reviewed
• [Journal Article] Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents (2010)
  • Author(s): Endo, K., Ogawa, M., Shibata, T.
  • Journal Title: Angew.Chem.Int.Ed. 49highlighted by Synfacts
  • Peer Reviewed
• [Journal Article] Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp3-Carbon in 1,1-Diborylalkanes at Room Temperature (2010)
  • Author(s): Kohei Endo, Takahiro Ohkubo, Munenao Hirokami, Takanori Shibata
  • Journal Title: Journal of the American Chemical Society Volume: 132 Pages: 11033-11035
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of Tetrasubstituted Alkenylboronates via 1,1-Organodiboronates (2010)
  • Author(s): Kohei Endo, Munenao Hirokami, Takanori Shibata
  • Journal Title: Journal of Organic Chemistry Volume: 75 Pages: 3469-3472
  • Peer Reviewed
• [Journal Article] Synthesis of 1,1-Organodiboronates via RhICI-Catalyzed Sequential Hydroboration of 1-Alkynes (2010)
  • Author(s): Kohei Endo, Munenao Hirokami, Takanori Shibata
  • Journal Title: Synlett Pages: 1331-1335
  • Peer Reviewed
• [Journal Article] Multinuclear Gatalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents (2010)
  • Author(s): Kohei Endo, Mika Ogawa, Takanori Shibata
  • Journal Title: Angewandte Chemie International Edition 49 Pages: 2410-2413
  • Peer Reviewed
• [Journal Article] Synthesis of 1,1-Organodiboronates via Rh^ICl-Catalyzed Sequential Hydroboration of 1-Alkynes (2009)
  • Author(s): Endo, K., Hirokami, M., Shibata, T.
  • Journal Title: Synlett Pages: 1331-1335
  • Peer Reviewed
• [Presentation] BINOL-PHOS配位子から調製される複核パラジウム錯体を用いる触媒的不斉開環反応の開発 (2011)
  • Author(s): 田中啓介, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-28
• [Presentation] BINOL-PHOS配位子から調製される複核パラジウム錯体を用いる触媒的不斉開環反応の開発 (2011)
  • Author(s): 田中啓介、遠藤恆平、柴田高範
  • Organizer: 日本化学会 第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-28
• [Presentation] BINOL-PHOS配位子から調製される複核銅錯体を用いる有機金属試薬の触媒的不斉共役付加反応の開発 (2011)
  • Author(s): 焼石さゆり, 浜田大輔, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] 複核金属錯体を用いる有機金属試薬の触媒的不斉共役付加反応におけるSPINOL配位子の開発 (2011)
  • Author(s): 浜田大輔, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] 1,1-ジボリル-2-シリルアルカンを用いた立体選択的多置換アリルシラン誘導体の合成 (2011)
  • Author(s): 坂本晶, 大久保貴弘, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] 1,1-ジボリル-2-シリルアルカンを用いた立体選択的多置換アリルシラン誘導体の合成 (2011)
  • Author(s): 坂本晶、大久保貴弘、遠藤恆平、柴田高範
  • Organizer: 日本化学会 第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] 複核金属錯体を用いる有機金属試薬の触媒的不斉共役付加反応におけるSPINOL配位子の開発 (2011)
  • Author(s): 浜田大輔、遠藤恆平、柴田高範
  • Organizer: 日本化学会 第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] BINOL-PHOS配位子から調製される複核銅錯体を用いる有機金属試薬の触媒的不斉共役付加反応の開発 (2011)
  • Author(s): 焼石さゆり、浜田大輔、遠藤恆平、柴田高範
  • Organizer: 日本化学会 第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] 室温条件下におけるsp^3炭素上での化学選択的・位置特異的な鈴木・宮浦クロスカップリング反応の開発 (2011)
  • Author(s): 大久保貴弘, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-26
• [Presentation] 室温条件下におけるsp3炭素上での化学選択的・位置特異的な鈴木・宮浦クロスカップリング反応の開発 (2011)
  • Author(s): 大久保貴弘、遠藤恆平、柴田高範
  • Organizer: 日本化学会 第91春季年会
  • Place of Presentation: 神奈川大学
  • Year and Date: 2011-03-26
• [Presentation] SPINOL-PHOSによる複核金属錯体を用いた有機金属試薬の触媒的共役付加反応の開発(poster) (2011)
  • Author(s): 浜田大輔, 遠藤恆平, 柴田高範
  • Organizer: The 2nd Symposium on Chiral Science & Technology : Mesochemistry & Chemical Wisdom
  • Place of Presentation: 早稲田大学西早稲田キャンパス(東京)
  • Year and Date: 2011-03-02
• [Presentation] Development of Metal-Linked Multinuclear Catalyst for Highly Efficient Catalytic Asymmetric Alkylation Reactions (2010)
  • Author(s): Kohei Endo, Mika Ogawa, Keisuke Tanaka, Daisuke Hamada, Sayuri Yakeishi, Takanori Shibata
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Honolulu
  • Year and Date: 2010-12-16
• [Presentation] Development of Metal-Linked Multinuclear Catalyst for Highly Efficient Catalytic Asymmetric Alkylation Reactions (2010)
  • Author(s): Kohei Endo, et al.
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Honolulu, Hawaii
  • Year and Date: 2010-12-15
• [Presentation] Multinuclear Catalyst Using SPINOL-PHOS for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc and Organoaluminum Reagents (poster) (2010)
  • Author(s): Daisuke Hamada, Kohei Endo, Takanori Shibata
  • Organizer: 7th Symposium on Chemical Approaches to Chirality
  • Place of Presentation: Tokyo University of Science (Tokyo)
  • Year and Date: 2010-09-29
• [Presentation] 金属連結複核錯体触媒による不斉反応開発 (2010)
  • Author(s): 遠藤恆平, 田中啓介, 浜田大輔, 焼石さゆり, 小川美香, 柴田高範
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学
  • Year and Date: 2010-09-17
• [Presentation] 金属連結複核錯体触媒による不斉反応開発 (2010)
  • Author(s): 遠藤恆平、田中啓介、浜田大輔、焼石さゆり、小川美香、柴田高範
  • Organizer: 第57回 有機金属化学討論会
  • Place of Presentation: 中央大学(東京)
  • Year and Date: 2010-09-17
• [Presentation] 金属連結型配位子を用いる有機アルミニウム試薬の同触媒による共役付加反応の不斉制御 (2010)
  • Author(s): 小川美香, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-27
• [Presentation] 銅触媒による有機亜鉛試薬の不斉共役付加反応;金属連結型配位子を用いる立体選択性反転の新手法 (2010)
  • Author(s): 浜田大輔, 小川美香, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-27
• [Presentation] 1,1-二置換ホウ酸エステルを用いた立体選択的多置換アルケニルホウ酸エステルの合成 (2010)
  • Author(s): 廣神宗直, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-27
• [Presentation] 金属連結型配位子を用いる有機アルミニウム試薬の銅触媒による共役付加反応の不斉制御 (2010)
  • Author(s): 小川美香、遠藤恒平、柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-27
• [Presentation] 銅触媒による有機亜鉛試薬の不斉共役付加反応:金属連結型配位子を用いる立体選択性反転の新手法 (2010)
  • Author(s): 浜田大輔、小川美香、遠藤恒平、柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-27
• [Presentation] 1,1-二置換ホウ酸エステルを用いた立体選択的多置換アルケニルホウ酸エステル (2010)
  • Author(s): 廣神宗直、遠藤恆平、柴田高範
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-27
• [Presentation] Metal-linked BINOLate complex for Highly Efficent Cu-catalyzed Asymmetric Conjugate Addition of Organozinc Reagents (poster) (2009)
  • Author(s): Mika Ogawa, Kohei Endo, Takanori Shibata
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2009
  • Place of Presentation: 高麗大学(韓国)
  • Year and Date: 2009-12-16
• [Presentation] Metal-Iinked BINOLate complex for Highly Efficient Cu-catalyzed Asymnetric Conjugate Addition of Organozinc Reagents (2009)
  • Author(s): 小川美香、遠藤恆平、柴田高範
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2009
  • Place of Presentation: 韓国ソウル特別市
  • Year and Date: 2009-12-16
• [Presentation] 複核金属分子触媒の設計:等価な反応活性点の同時多発制御 (2009)
  • Author(s): 遠藤恆平
  • Organizer: 若手研究者のためのセミナー,有機合成化学協会関東支部
  • Place of Presentation: 東京大学
  • Year and Date: 2009-12-12
• [Presentation] 複核金属分子触媒の設計:等価な反応活性点の同時多発制御 (2009)
  • Author(s): 遠藤恆平
  • Organizer: 有機合成化学協会関東支部若手研究者のためのセミナー
  • Place of Presentation: 東京大学
  • Year and Date: 2009-12-12
• [Presentation] BINOL Scaffold for Metal-linked ligand in Highly Efficient Cu-catalyzed Asymmetric Conjugate Addition of Organozinc Reagents (poster) (2009)
  • Author(s): Mika Ogawa, Kohei Endo, Takanori Shibata
  • Organizer: IKCOC 11
  • Place of Presentation: Rihga Royal Hotel Kyoto
  • Year and Date: 2009-11-10
• [Presentation] 1,1-二置換ホウ酸エステルを用いた立体選択的多置換アルケニルホウ酸エステルの合成(poster) (2009)
  • Author(s): 廣神宗直, 遠藤恆平, 柴田高範
  • Organizer: 第96回有機合成シンポジウム
  • Place of Presentation: 早稲田大学国際会議場(東京)
  • Year and Date: 2009-11-06
• [Presentation] 金属連結型テトラホスフィン配位子を用いるパラジウム触媒による酸無水物の不斉非対称化反応の開発(poster) (2009)
  • Author(s): 田中啓介, 小川美香, 遠藤恆平, 柴田高範
  • Organizer: 日本化学会第3回関東支部大会
  • Place of Presentation: 早稲田大学(東京)
  • Year and Date: 2009-09-04
• [Presentation] 金属連結型テトラホスフィン配位子を用いる銅触媒による有機亜鉛試薬の立体選択的共役付加反応の開発 (2009)
  • Author(s): 遠藤恆平, 小川美香, 柴田高範
  • Organizer: 日本化学会第3回関東支部大会
  • Place of Presentation: 早稲田大学(東京)
  • Year and Date: 2009-09-04
• [Presentation] 金属連結型テトラホスフィン配位子を用いる銅触媒による有機亜鉛試薬の立体選択的共役付加反応の開発 (2009)
  • Author(s): 還藤恆平、小川美香、柴田高範
  • Organizer: 日本化学会第3回関東支部大会
  • Place of Presentation: 早稲田大学
  • Year and Date: 2009-09-04
• [Presentation] Development of Metal-Linked Molecular Catalyst (2009)
  • Author(s): 遠藤恆平
  • Organizer: Intornational Symposium on Chiral Compounds and Special Polymers(CCSP)
  • Place of Presentation: 中国哈爾浜市
  • Year and Date: 2009-07-14
• [Presentation] Development of Metal-Linked Molecular Catalyst (2009)
  • Author(s): Kohei Endo
  • Organizer: International Symposium on Chiral Compounds and Special Polymers (CCSP)
  • Place of Presentation: Harbin, China
• [Remarks] ホームページ等
  • URL: http://www.endorg.com/
• [Remarks]
  • URL: http://www.endorg.com/