Development of Highly Practical Process of Organic Synthesis by using Asymmetric Organocatalysts

• Project/Area Number: 21890112
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Kyoto University
• Principal Investigator: INOKUMA Tsubasa Kyoto University, 薬学研究科, 特定助教 (40541272)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥2,652,000 (Direct Cost: ¥2,040,000、Indirect Cost: ¥612,000); Fiscal Year 2010: ¥1,261,000 (Direct Cost: ¥970,000、Indirect Cost: ¥291,000); Fiscal Year 2009: ¥1,391,000 (Direct Cost: ¥1,070,000、Indirect Cost: ¥321,000)
• Keywords: 有機触媒 / 不斉反応 / ペタシス反応 / アミノ酸 / 不斉有機触 / チオ尿素 / β,γ-不飽和アミノ酸 / 不斉有機触媒

Research Abstract

We developed the novel hydrogen bond donor catalysts such as quinazolines, benzothiadiazines and hydroxyl thiourea catalysts. By using these new catalysts, we succeeded in synthesizing the pharmacologically important compounds such as optically active allenes or the oligo peptides which contain the unnatural amino acid moieties.

Research Products

• [Journal Article] Synthesis of Optically Active N-Aryl Amino Acid Derivatives through the Asymmetric Petasis Reaction Catalyzed by Novel Hydroxy-thiourea (2011)
  • Author(s): T.Inokuma, Y.Suzuki, Y.Takemoto
  • Journal Title: Chem.Asian.J 印刷中
• [Journal Article] Bronsted Acid-Thiourea Co-catalysis : Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from α-Enaminoesters and α, β-Unsaturated Aldehydes. (2010)
  • Author(s): K.Yoshida, T.Inokuma, K.Takasu, Y.Takemoto
  • Journal Title: Synlett Pages: 1865-1865
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Synthesis of Both Enantiomers of 4 Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions. (2010)
  • Author(s): K.Yoshida, T.Inokuma, K.Takasu, Y.Takemoto
  • Journal Title: Molecules 15 Pages: 8305-8305
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Synthesis of Both Enantiomers of 4 Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions. (2010)
  • Author(s): 吉田耕三、猪熊翼、高須清誠、竹本佳司
  • Journal Title: Molecules Volume: 15 Pages: 8305-8326
  • Peer Reviewed
• [Journal Article] Bronsted Acid-Thiourea Co-catalysis : Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from α-Enaminoesters and α,β-Unsaturated Aldehydes. (2010)
  • Author(s): 吉田耕三、猪熊翼、高須清誠、竹本佳司
  • Journal Title: Synlett Pages: 1865-1869
  • Peer Reviewed
• [Journal Article] Asymmetric Synthesis of 4-Substituted 2,6-Dioxopiperidine-3-carbonitrile by Using Thiourea-Catalyzed Asymmetric Michael Addition. (2009)
  • Author(s): T.Inokuma, Y.Nagamoto, S.Sakamoto, H.Miyabe, K.Takasu, Y.Takemoto
  • Journal Title: Heterocycles 79 Pages: 573-573
  • NAID: 40016543089
  • Peer Reviewed
• [Journal Article] Enantioselective nitrocyclopropanation of α, β-unsaturated α-cyanoimides catalyzed by bifunctional thiourea. (2009)
  • Author(s): T.Inokuma, S.Sakamoto, Y.Takemoto
  • Journal Title: Synlett Pages: 1627-1627
  • NAID: 120001479076
  • Peer Reviewed
• [Journal Article] Hydroxyl Group-Directed Organocatalytic Asymmetric Michael Addition of α, β-Unsaturated Ketones with Alkenylboronic Acids (2009)
  • Author(s): T.Inokuma, K.Takasu, T.Sakaeda, Y.Takemoto
  • Journal Title: Org.Lett. 11 Pages: 2425-2425
  • Peer Reviewed
• [Journal Article] Hydroxy Group-Directed Organocatalytic Asymmetric Michael Addition of α, β-Unsaturated Ketones with Alkenylboronic Acids (2009)
  • Author(s): 猪熊翼, 高須清誠, 栄田敏之, 竹本佳司
  • Journal Title: Org.Lett. 11 Pages: 2425-2428
  • Peer Reviewed
• [Presentation] チオ尿素触媒を用いた有機ホウ酸試薬の不斉付加反応の開発 (2010)
  • Author(s): 猪熊翼
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: ウインクあいち(名古屋)
  • Year and Date: 2010-11-02
• [Presentation] チオ尿素触媒を用いた有機ホウ酸試薬の不斉付加反応の開発 (2010)
  • Author(s): 猪熊翼、鈴木雄介、竹本佳司
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 名古屋
• [Presentation] 新規チオ尿素触媒を用いた不斉ペタシス反応の開発 (2010)
  • Author(s): 猪熊翼,栄田敏之,竹本佳司
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Book] 進化を続ける有機触媒 (2009)
  • Author(s): 竹本佳司,猪熊翼
  • Publisher: 化学同人
• [Remarks] ホームページ等
  • URL: http://www.pharm.kyoto-u.ac.jp/orgchem/
• [Remarks]
  • URL: http://www.pharm.kyoto-u.ac.jp/orgchem/
• [Remarks]
  • URL: http://www.pharm.kyoto-u.ac.jp/orgchem/