Development of the Catalytic Asymmetric Multi-component Reactions

• Project/Area Number: 20850017
• Research Category: Grant-in-Aid for Young Scientists (Start-up)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: SOETA Takahiro Kanazawa University, 物質化学系, 助教 (10506819)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥3,276,000 (Direct Cost: ¥2,520,000、Indirect Cost: ¥756,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥1,716,000 (Direct Cost: ¥1,320,000、Indirect Cost: ¥396,000)
• Keywords: 多成分反応 / イソシアニド / 触媒的不斉反応 / 不斉反応

Research Abstract

1)TMSC1を用いた環状ニトロンへのイソシアニドの付加反応の開発
TMSC1存在下、イソシアニドの環状ニトロンへの付加反応を行ったところ、対応するテトラヒドロイソキノリン骨格を有するアミドを良好な収率で得ることができた。本反応はTMSC1非存在化では進行しないことを確認した。
2)アルデヒド、イソシアニドおよびシラノールを用いたPasserini型反応の開発
シラノール存在下、アルデヒドへのイソシアニドの付加反応を行ったところ、対応するα-siloxyamide誘導体を高収率で得た。本手法はα-siloxyamide誘導体をone-potで効率よく得ることが可能な数少ない例の一つである。
以上のように本研究者は、イソシアニドの付加反応を鍵とする、新規反応の開発に成功した。これらの研究で得られた知見を活かし、新規かつ高効率的な不斉反応の開発に期待できる。

Research Products

• [Journal Article] Diastereoselective Cycloadditions Using Chiral Oxzolidinones Without Lewis Acid. (2009)
  • Author(s): Mukund P. Sibi, Takahiro Soeta, Craig P. Jasperse. Nitrile Ylides
  • Journal Title: Org. Lett. 11 Pages: 5366-5369
  • Peer Reviewed
• [Journal Article] ChiralAmidophosphane-Rhodium(I)-Catalyzed Asymmetric Conjugate Arylation of Acyclic Enones with Arylboronic Acids. (2009)
  • Author(s): Qian Chen, Masami Kuriyama, Xinyu Hao, Takahiro Soeta, Yasutomo Yamamoto, Ken-ichi Yamada, KiyoshiTomioka.
  • Journal Title: Chem. Pharm. Bull. 57 Pages: 1024-1027
  • NAID: 130000124206
  • Peer Reviewed
• [Journal Article] Nitrile Ylides : Diastereoselective Cycloadditions Using Chiral Oxzolidinones Without Lewis Acid. (2009)
  • Author(s): Mukund P.Sibi, Takahiro Soeta, Craig J.Jasperse
  • Journal Title: Organic letters 11 Pages: 5366-5369
  • Peer Reviewed
• [Journal Article] Chiral Amidophosphane-Rhodium(I)-Catalyzed Asymmetric Conjugate Arylation of Acyclic Enones with Arylboronic Acids. (2009)
  • Author(s): Qian Chen, Masami Kuriyama, Xinyu Hao, Takahiro Soeta, Yasutomo Yamamoto, Ken-ichi Yamada, Kiyoshi Tomioka
  • Journal Title: Chemical and Pharmaceutical Bulletine 57 Pages: 1024-1027
  • NAID: 130000124206
  • Peer Reviewed
• [Journal Article] Small-Molecule CD4 Mimics Interact with a Highly Conserved Pocket on HIV-1 gp 120. (2008)
  • Author(s): Navid Madani, Arne Schon, Amy M. Princitto, Judith M. LaLonde, Joel R. Coueter, Takahiro Soeta, Danny Ng, Lipig Wang, Evan T. Brower, Shi-Hua Xiang, Young Do Kwon, Chih-chi Huang, Richard Wyatt, Peter D. Kwong, Ernest Freire, Amos B. Smith III, Joseph, SoNavid Ma
  • Journal Title: Structure 16 Pages: 1689-1701
  • Peer Reviewed
• [Journal Article] Copper(II) Catalyzed Exo and Enantioselectice Cycloaddition of Azomethine imines. (2008)
  • Author(s): Mukund P. Sibi, Digamber Rane, Levi M. Stanley, Takahiro Soeta
  • Journal Title: Org. Lett. 10 Pages: 2971-2974
  • Peer Reviewed
• [Journal Article] Amidophosphane-Copper(I)-Catalyz ed Asymmetric Conjugate Addition of Dialkylzinc Reagents to Racemic 6-Substituted Cyclohexenones to Form 2, 5-Di-and 2, 2, 5-Trisubstituted Cyclohexanones. (2008)
  • Author(s): Khalid Selim, Takahiro Soeta, Ken-ichi Yamada, Kiyoshi Tomioka.
  • Journal Title: Chem. Asian. J. 3 Pages: 342-350
  • Peer Reviewed
• [Journal Article] Small-Molecule CD4 Mimics Interact with a Highly Conserved Pocket on HIV-1 gp 120. (2008)
  • Author(s): Navid Madani, Takahiro Soeta, Amos B. Smith III, et al
  • Journal Title: Structure 16 Pages: 1689-1701
  • Peer Reviewed
• [Journal Article] Copper(II)-Catalyzed Exo and Enantioselective Cycloaddition of Azomethine Imines. (2008)
  • Author(s): Mukund P. Sibi, Takahiro Soeta, et al
  • Journal Title: Organic Letters 10 Pages: 2971-2974
  • Peer Reviewed
• [Presentation] TMSClを用いたイソシアニドのニトロンへの付加反応の開発。 (2010)
  • Author(s): 添田貴宏、杉山博一、宇梶裕、猪股勝彦
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] アルデヒド、イソシアニド、シラノールを用いたPasserini型反応の開発。 (2010)
  • Author(s): 小嶋優樹、添田貴宏、宇梶裕、猪股勝彦
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学(大阪)
  • Year and Date: 2010-03-29
• [Presentation] TMSC1を用いたイソシアニドのニトロンへの付加反応の開発 (2010)
  • Author(s): 添田貴宏、杉山博一、宇梶裕、猪股勝彦
  • Organizer: 日本化学会 第90春期年会
  • Place of Presentation: 近畿大学(大阪府)
  • Year and Date: 2010-03-29
• [Presentation] アルデヒド、イソシアニド、シラノールを用いたPasserini型反応の開発 (2010)
  • Author(s): 小嶋優樹、添田貴宏、宇梶裕、猪股勝彦
  • Organizer: 日本化学会 第90春期年会
  • Place of Presentation: 近畿大学(大阪府)
  • Year and Date: 2010-03-29
• [Presentation] Enantioselective Conjugate Addition of Hydrazines to -Unsaturated Imides. (2008)
  • Author(s): Takahiro Soeta, Mukund P. Sibi.
  • Organizer: Synthesis of Chiral Pyrazolidinones. 1st International Synposium on Process Chemistry.
  • Place of Presentation: 京都国際会館(京都)
  • Year and Date: 2008-07-30
• [Presentation] Enantioselective Conjugate Addition of Hydradines to α, β-Unsaturated Imides. Synthesis of Chiral Pyrazolidinones. (2008)
  • Author(s): 添田貴宏
  • Organizer: The First International Symposium on Process Chemistry
  • Place of Presentation: 京都
  • Year and Date: 2008-07-30
• [Remarks] 招待講演日本薬学会東海支部特別講演会「高立体選択的含窒素複素環構築反応の開発」2008年12月10日、岐阜薬科大学(岐阜)