Organic superbase/lithium salt-cooperative catalyst system

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K08229
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Doshisha Women's College of Liberal Arts
• Principal Investigator: Yamamoto Yasutomo 同志社女子大学, 薬学部, 准教授 (10452278)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: 有機強塩基 / ヒドロアミノ化

Outline of Final Research Achievements

Organic Superbase-catalyzed intramolecular hydroamination of aminoalkenes was examined. Phosphazene t-Bu P4 base effectively catalyzed the hydroamination to give cyclized product in good yield. High basicity of phosphazene catalyst was essential for this reaction, and normal organic bases did not catalyze the reaction. Although this reaction required high reaction temperature and long reaction time, various aminoalkenes were applicable. We also found that microwave irradiation dramatically shortened the reaction time. Phosphazene catalyst system was also applicable to an intramolecular hydroalkoxylation of hydroxyalkenes.

Free Research Field

化学系薬学

Academic Significance and Societal Importance of the Research Achievements

本反応の意義の一つは、生物活性化合物に良く見られる複素環の簡便な触媒的合成法になり得るという点である。アルケンに対する分子内アミンの付加反応では窒素複素環が、アルコールの付加反応では酸素複素環が構築できる。本法により、生物活性化合物に良く見られるイソキノリン、イソインドリン、イソベゾフラン骨格を構築できる。また、金属フリーのアニオン種の反応性を評価できる点も大きな特徴である。