Creation of Functionalized Chiral Heterobidentate Ferrocene Ligands bearing a Heterocyclic Group and Their Catalysis

• Project/Area Number: 22550044
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Chuo University
• Principal Investigator: FUKUZAWA Shinichi 中央大学, 理工学部, 教授 (50173331)
• Co-Investigator(Renkei-kenkyūsha): OGATA Kenichi 中央大学, 理工学部, 助教 (60431970)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2010: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: フェロセン / 不斉触媒 / ヘテロ環 / 異原子配位子 / 環化付加反応 / 共役付加反応アゾメチンイリド / 有機化学 / 合成化学 / 不斉合成 / クリックケミストリー / ThioClickFerrophos / アゾメチンイリド / 1, 3-双極子環化付加 / P, S-配位子 / プロリン / Mannich反応

Research Abstract

Chiral ferrocenyl hetero-bidentate ligand, ThioClickFerrophos was newly prepared. The complex of silver acetate with ThioClickFerrophos was efficient catalyst for the reaction using glycine imino ester as a starting compound. Thus, it cata

Research Products

• [Journal Article] Stereochemistry of Substitution of the α-Dimethylamino Group by Dialkylzinc in ChiralBenzylferrocene (2012)
  • Author(s): T. Takahashi, K. Ogata, S. Fukuzawa
  • Journal Title: J. Org. Chem Volume: 77 Pages: 6638-6642
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands (2012)
  • Author(s): T. Konno, K. Shimizu, K. Ogata, S. Fukuzawa
  • Journal Title: J. Org. Chem Volume: 77 Pages: 3318-3324
  • Peer Reviewed
• [Journal Article] Silver/ThioClickFerrophos-Catalyzed Enantioselective Conjugate Addition and Cycloaddition of Glycine Imino Ester with Nitroalkenes (2012)
  • Author(s): K. Imae, T. Konno, K. Ogata, S. Fukuzawa
  • Journal Title: Org. Lett Volume: 14 Pages: 4410-4413
  • Peer Reviewed
• [Journal Article] Stereochemistry of Substitution of the alpha-Dimethylamino Group by Dialkylzinc in Chiral Benzylferrocene (2012)
  • Author(s): T. Takahashi, T. Konno, K. Ogata, S. Fukuzawa (T. Takahashi)
  • Journal Title: J. Org. Chem. Volume: 77 Issue: 15 Pages: 6638-6642
  • DOI: 10.1021/jo3012013
  • Peer Reviewed
• [Journal Article] Direct C-H Carboxylation with Carbon Dioxide Using 1,2,3-Triazol-5-ylidene Copper(I) Complexes (2012)
  • Author(s): H. Inomata
  • Journal Title: Org. Lett. Volume: 14 Issue: 15 Pages: 3986-3989
  • DOI: 10.1021/ol301760n
  • Peer Reviewed
• [Journal Article] Synthetic, Structural, and Catalytic Studies of Well-Defined Allyl 1,2,3-Triazol-5-ylidene (tzNHC) Palladium Complexes (2012)
  • Author(s): T. Terashima, S. Inomata, K. Ogata, S. Fukuzawa (T. Terashima)
  • Journal Title: Eur. J. Inorg. Chem. Volume: 2012 Issue: 9 Pages: 1387-1393
  • DOI: 10.1002/ejic.201101383
  • Peer Reviewed
• [Journal Article] Copper(I) 1,2,3-Triazol-5-ylidene Complexes as Efficient Catalysts for Click Reactions of Azides with Alkynes (2011)
  • Author(s): T . Nakamura, T. Terashima, K. Ogata, S. Fukuzawa
  • Journal Title: Org. Lett Volume: 13 Pages: 620-623
  • Peer Reviewed
• [Journal Article] Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base (2011)
  • Author(s): K. Imae, K. Shimizu, K. Ogata, S. Fukuzawa
  • Journal Title: J. Org. Chem Volume: 76 Pages: 3604-3608
  • Peer Reviewed
• [Journal Article] Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base (2011)
  • Author(s): Imae, K, Shimizu, K Ogata, K, Fukuzawa, S
  • Journal Title: J. Org. Chem. Volume: 76 Issue: 9 Pages: 3604-3608
  • DOI: 10.1021/jo2003727
  • Peer Reviewed
• [Journal Article] 1,2,3-Triazol-5-ylidene-palladium complex catalyzed Mizoroki-Heck and Sonogashira coupling reactions (2011)
  • Author(s): Inomata, S, Hiroki, H, Terashima, T, Ogata, K, Fukuzawa, S
  • Journal Title: TETRAHEDRON Volume: 67 Issue: 38 Pages: 7263-7267
  • DOI: 10.1016/j.tet.2011.07.045
  • Peer Reviewed
• [Journal Article] Copper(I) 1,2,3-Triazol-5-ylidene Complexes as Efficient Catalysts for Click Reactions of Azides with Alkynes (2011)
  • Author(s): Nakamura, T, Terashima, T, Ogata, K, Fukuzawa, S
  • Journal Title: Org. Lett. Volume: 13 Issue: 4 Pages: 620-623
  • DOI: 10.1021/ol102858u
  • Peer Reviewed
• [Journal Article] Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with α-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex (2010)
  • Author(s): I. Oura, K. Shimizu, K. Ogata, S. Fukuzawa
  • Journal Title: Org. Lett Volume: 39 Pages: 1752-1755
  • Peer Reviewed
• [Journal Article] Ag/ThioClickFerrophos catalyzed highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides with alkenes (2010)
  • Author(s): K. Shimizu, K. Ogata, S. Fukuzawa
  • Journal Title: Tetrahedron Lett Volume: 51 Pages: 5068-5070
  • Peer Reviewed
• [Journal Article] Ag/ThioClickFerrophos catalyzed highly enantioselective 1,3-dipolar cyclo addition of azomethine ylides with alkenes (2010)
  • Author(s): K.Shimizu, K.Ogata, S.Fukuzawa
  • Journal Title: Tetrahedron Letters Volume: 51 Pages: 5068-5070
  • Peer Reviewed
• [Journal Article] Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with alpha-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex (2010)
  • Author(s): I.Oura, K.Shimizu, K.Ogata, S.Fukuzawa
  • Journal Title: Organic.Letters Volume: 12 Pages: 1752-1755
  • Peer Reviewed
• [Journal Article] Synthesis of Dichloro bis(1,4-dimesityl-1H-1,2,3-triazol-5-ylidene)palladium [PdCl_2(TMes)_2] and Its Application to Suzuki-Miyaura Coupling Reaction (2010)
  • Author(s): T.Nakamura, K.Ogata, S.Fukuzawa
  • Journal Title: Chemistry Letters Volume: 39 Pages: 920-923
  • NAID: 10027184458
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Ring-Opening Three-Component Coupling of Methylene cyclopropane with Aldehydes and Silanes (2010)
  • Author(s): K.Ogata, Y.Atsuumi, S.Fukuzawa
  • Journal Title: Organic.Letters Volume: 12 Pages: 4536-4539
  • Peer Reviewed
• [Presentation] 二官能性触媒酢酸銀/ThioClickFerrophos 錯体を用いるアゾメチンイリドと電子不足アルケンとの不斉 1,3‐ 双極子環化付加反応 (2013)
  • Author(s): 渡部紗世,徳光千尋,紺野貴史, 緒方賢一・福澤信一
  • Organizer: 日本化学会第93 春季年会
  • Place of Presentation: 立命館大学,草津
  • Year and Date: 2013-03-22
• [Presentation] 銀(I)/ThioClickFerrophos 錯体触媒を用いるグリシンイミノエステルと α,β-不飽和エステルとの不斉共役付加反応 (2012)
  • Author(s): 紺野貴史,緒方賢一,福澤信一
  • Organizer: 第64回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 長岡技術科学大学,長岡
  • Year and Date: 2012-12-01
• [Presentation] Asymmetric Conjugate Addition of Glycine Imine to Nitroalkenes catalyzed by Ag/ThioClickFerrophos Complex (2012)
  • Author(s): Shin-ichi Fukuzawa
  • Organizer: Cambodian Malaysian Chemical Conference
  • Place of Presentation: シェムリアップ,カンボジア
  • Year and Date: 2012-10-19
• [Presentation] Silver ThioClickFerrophos-Catalyzed Enantioselective conjugate Addition and Cycloaddition ofGlycine Schiff Base with Nitroalkenes (2012)
  • Author(s): Takashi Konno, Kazumi Imae, Kenichi Ogata,Shin-ichi Fukuzawa
  • Organizer: International Conference on Organometallic Chemistry
  • Place of Presentation: リスボン,ポルトガル
  • Year and Date: 2012-09-07
• [Presentation] ビニルセレノンとアゾメチンイリドとの 1,3-双極子環化付加反応を経るピロール合成 (2012)
  • Author(s): 渡部紗世,緒方賢一,福沢信一
  • 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,野田
  • Year and Date: 2012-05-19
• [Presentation] 光学活性アミノフェロセンの alpha 位置換反応の立体化学の再検証 (2012)
  • Author(s): 高橋樹生,福沢信一,緒方賢一
  • 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,野田
  • Year and Date: 2012-05-19
• [Presentation] 新型ClickFerrophos -ロジウム錯体を用いるα,β-不飽和リン酸エステルの不斉水素化反応 (2012)
  • Author(s): 紺野貴史・緒方賢一・ 福澤信一
  • Organizer: 日本化学会第92 春季年会
  • Place of Presentation: 慶應義塾大学,日吉
  • Year and Date: 2012-03-26
• [Presentation] Silver ThioClickFerrophos-Catalyzed Enantioselective conjugate Addition and Cycloaddition of Glycine Schiff Base with Nitroalkenes (2012)
  • Author(s): akashi Konno, Kazumi Imae, Kenichi Ogata, Shin-ichi Fukuzawa (Takashi Konno)
  • Organizer: International Conference on Organometallic Chemistry
  • Place of Presentation: リスボン，ポルトガル
• [Presentation] Asymmetric Conjugate Addition of Glycine Imine to Nitroalkenes catalyzed by Ag/ThioClickFerrophos Complex (2012)
  • Author(s): Shin-ichi Fukuzawa
  • Organizer: Cambodian Malaysian Chemical Conference
  • Place of Presentation: シェムリアップ，カンボジア
  • Invited
• [Presentation] 光学活性アミノフェロセンのalpha位置換反応の立体化学の再検証 (2012)
  • Author(s): 高橋樹生，福沢信一，緒方賢一（高橋樹生）
  • 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（野田キャンパス）
• [Presentation] ビニルセレノンとアゾメチンイリドとの 1,3-双極子環化付加反応を経るピロール合成 (2012)
  • Author(s): 渡部紗世，緒方賢一，福沢信一
  • 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（野田キャンパス）
• [Presentation] 紺野貴史、緒方賢一、福澤信一(紺野貴史） (2012)
  • Author(s): 銀(I)/ThioClickFerrophos錯体触媒を用いるグリシンイミノエステルとα,β-不飽和エステルとの不斉共役付加反応（
  • Organizer: 第６４回有機合成化学協会関東支部シンポジウム
  • Place of Presentation: 長岡技術科学大学
• [Presentation] 新型ClickFerrophos－ロジウム錯体を用いるalpha,beta-不飽和リン酸エステルの不斉水素化反応 (2012)
  • Author(s): 紺野 貴史・緒方 賢一・福澤 信一
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 慶應義塾大学
• [Presentation] 1,2,3-トリアゾールカルベン銅錯体を用いるアゾール類と二酸化炭素との反応 (2012)
  • Author(s): 猪俣 宏・緒方 賢一・福澤 信一・侯 召民
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 慶應義塾大学
• [Presentation] Synthesis of Palladium 1,2,3-Triazol-5-ylidene Complexes and Their Catalysis in Coupling Reactionswith Aryl Halides (2011)
  • Author(s): S. Fukuzawa, T. Terashima
  • Organizer: XIX EuCheMS Conference on Organometallic Chemistry
  • Place of Presentation: トゥルーズ,フランス
  • Year and Date: 2011-07-05
• [Presentation] ClickFerrophos/銀錯体触媒を用いるイミノエステルの不斉 α-アミノ化反応および Mannich反応 (2011)
  • Author(s): 今榮麗仁,緒方賢一, 福澤信一
  • Organizer: 日本化学会第91 春季年会
  • Place of Presentation: 神奈川大学,横浜
  • Year and Date: 2011-03-29
• [Presentation] ClickFerrophos/銀錯体触媒を用いるイミノエステルの不斉α-アミノ化反応およびMannich反応 (2011)
  • Author(s): 今榮麗仁, 緒方賢一, 福澤信一
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学,横浜
  • Year and Date: 2011-03-29
• [Presentation] Synthesis of Palladium 1,2,3-Triazol-5-ylidene Complexes and Their Catalysis in Coupling Reactions with Aryl Halides (2011)
  • Author(s): Fukuzawa S, Terashima, T.
  • Organizer: XIX EuCheMS Conference on Organometallic Chemistry
  • Place of Presentation: Toulouse, France
• [Presentation] Preparation of new ClickFerrophos ligands and their application to asymmetric synthesis (2010)
  • Author(s): K. Imae, K. Shimizu, K. Ogata, S. Fukuzawa
  • Organizer: PACHIFICHEM2010
  • Place of Presentation: ホノルル,USA
  • Year and Date: 2010-12-17
• [Presentation] Asymmetric C-C-Bond Formation by Ag and Cu/ClickFerrophos Ligands (2010)
  • Author(s): K. Shimizu, K. Imae, K. Ogata, S. Fukuzawa
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学,八王子
  • Year and Date: 2010-09-17
• [Presentation] Nickel(0)-Catalyzed Three Component Coupling of Methylenecyclopropanes with Aldehydes and Silanes (2010)
  • Author(s): Y.Atsuumi, K.Ogata, S.Fukuzawa
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学,八王子
  • Year and Date: 2010-09-17
• [Remarks]
  • URL: http://www.chem.chuo-u.ac.jp/~fukuzawaweb/index.html
• [Remarks] 中央大学理工学部応用化学科新触媒有機反応研究室
  • URL: http://www.chem.chuo-u.ac.jp/~fukuzawaweb/index.html
• [Remarks] 中央大学理工学部応用化学科新触媒有機反応研究室
  • URL: http://www.chem.chuo-u.ac.jp/~fukuzawaweb/index.html
• [Remarks]
  • URL: http://www.chem.chuo-u.ac.jp/~fukuzawaweb/index.html