Development of efficient and sequential bond-forming reaction using diverse reactivity of conjugated imines

• Project/Area Number: 20790023
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Kobe Pharmaceutical University
• Principal Investigator: UEDA Masafumi Kobe Pharmaceutical University, 薬学部, 講師 (00340935)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 合成化学 / ラジカル反応 / 共役イミン / ヒドロキシアルキル化 / 酸化 / トリエチルボラン / ドミノ反応 / ヒドロキシスルフィド / チオール

Research Abstract

We are interested in the diverse reactivity of conjugated imines and successfully developed novel domino reactions involving regioselective radical addition reaction and subsequent hydroxylation with aerobic oxygen. Hydoxysulfenylation reaction via carbon-sulfur bond formation and hydroxylation and Hydoxyalkylation reaction via carbon-carbon bond formation and hydroxylation have been developed.

Research Products

• [Journal Article] Aerobic Hydroxylation of N-Borylenamine: Triethylborane-mediated Hydroxyalkylation of α, β-Unsaturated Oxime Ether. (2009)
  • Author(s): Ueda, M.; Miyabe, H.; Kimura, T.; Kondoh, E.; Naito, T.; Miyata, O.
  • Journal Title: Org. Lett. 11 Pages: 4632-4635
  • Peer Reviewed
• [Journal Article] Two Novel Domino Reactions Triggered by Thiyl-Radical Addition to Vinylcyclopropyl Oxime Ether. (2009)
  • Author(s): Rahaman, H.; Ueda, M.; Miyata, O.; Naito, T.
  • Journal Title: Org. Lett. 11 Pages: 2651-2654
  • Peer Reviewed
• [Journal Article] Carbon Radical Addition to N-Sulfonylimines Mediated by Triethylborane or Zinc. (2009)
  • Author(s): Ueda, M.; Miyabe, H.; Miyata, O.; Naito, T.
  • Journal Title: Tetrahedron 65 Pages: 1321-1326
  • Peer Reviewed
• [Journal Article] Intermolecular Carbon Radical Addition to Cyclic Nitrone. (2009)
  • Author(s): Ueda, M.; Miyabe, H.; Nonoguchi, N.; Miyata, O.; Naito, T.
  • Journal Title: Heterocycles 79 Pages: 739-751
  • NAID: 40016543103
  • Peer Reviewed
• [Journal Article] Carbon Radical Addition to N-Sulfonylimines Mediated by Triethylborane or Zinc (2009)
  • Author(s): 上田昌史
  • Journal Title: Tetrahedron 65 Pages: 1321-1326
  • Peer Reviewed
• [Journal Article] Two Novel Domino Reactions Triggered by Thiyl-Radical Addition to Vinylcyclopropyl Oxime Ether (2009)
  • Author(s): Habibur Rahaman
  • Journal Title: Org.Lett. 11 Pages: 2651-2654
  • Peer Reviewed
• [Journal Article] Aerobic Hydroxylation of N-Borylenamine : Triethylborane-mediated Hydroxyalkylation of α, β-Unsaturated Oxime Ether (2009)
  • Author(s): 上田昌史
  • Journal Title: Org.Lett. 11 Pages: 4632-4635
  • Peer Reviewed
• [Journal Article] Regioselective Hydroxysulfenylation of α, β-Unsaturated Imines: Stability of Intermediate Radical Enhanced by Imino Group. (2008)
  • Author(s): Ueda, M.; Miyabe, H.; Shimizu, H.; Sugino, H.; Miyata, O.; Naito, T.
  • Journal Title: Angew. Chem. Int. Ed. 47 Pages: 5600-5604
  • Peer Reviewed
• [Journal Article] Regioselective Hydroxysulfenylation of α, β-Unsaturated Imines : Enhanced Stability of an Intermediate Radical (2008)
  • Author(s): 上田昌史
  • Journal Title: Angew. Chem. Int. Ed 47 Pages: 5600-5604
  • Peer Reviewed
• [Journal Article] Novel Synthesis of Substituted Pyrrolidines and Piperidines via Radical Addition-Ionic Cyclization Reaction of Oxime Ethers (2008)
  • Author(s): 宮田興子
  • Journal Title: Tetrahedron 64 Pages: 1270-1284
  • Peer Reviewed
• [Journal Article] Formal Alder-ene Reaction of a Bicyclo[1.1.0]butane in the Synthesis of the Tricyclic Quaternary Ammonium Core of Daphniglaucins (2008)
  • Author(s): 上田昌史
  • Journal Title: Tetrahedron Lett 49 Pages: 5986-5989
  • Peer Reviewed
• [Presentation] Hydroxyalkylation of α, β-Unsaturated oxime ether (2009)
  • Author(s): Ueda M., Naito T., Miyata O.
  • Organizer: 4th Pacific Symposium on Radical Chemistry
  • Place of Presentation: Shanghai
  • Year and Date: 2009-11-20
• [Presentation] 共役イミン類のヒドロキシスルフィド化およびヒドロキシアルキル化反応の開発 (2009)
  • Author(s): 上田昌史、清水秀憲、木村隆浩、近藤瑛子、内藤猛章、宮田興子
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
  • Year and Date: 2009-11-17
• [Presentation] アルキニルオキシムエーテル類への位置特異的共役付加反応の開発 (2008)
  • Author(s): 上田昌史、吉田勤一、池田祐紀、宮田興子、宮部豪人、内藤猛章
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2008-11-04
• [Presentation] 共役オキシムエーテル類への位置選択的ラジカル付加反応 : 水酸基導入反応への展開 (2008)
  • Author(s): 内藤猛章
  • Organizer: 第58回日本薬学会近畿支部総会・大会
  • Place of Presentation: 神戸
  • Year and Date: 2008-10-25
• [Presentation] Domino Radical Reaction of α, β-Unsaturated Oxime Ether (2008)
  • Author(s): Ueda M., Miyabe H., Miyata O., Naito T.
  • Organizer: The Fifth International Symposium on Integrated Synthesis
  • Place of Presentation: Kobe
  • Year and Date: 2008-09-05