Control of short-lived highly reactive carbocation species for drug discovery and life science applications

2020 Fiscal Year Final Research Report

• Project/Area Number: 19K22489
• Research Category: Grant-in-Aid for Challenging Research (Exploratory)
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 47:Pharmaceutical sciences and related fields
• Research Institution: Kanazawa University
• Principal Investigator: KUNISHIMA MUNETAKA 金沢大学, 薬学系, 教授 (10214975)
• Co-Investigator(Kenkyū-buntansha): 藤田 光 金沢大学, 薬学系, 助教 (40782850)
• Project Period (FY): 2019-06-28 – 2021-03-31
• Keywords: カルボカチオン / 一分子脱離反応 / アルキル化反応 / トリアジン及び誘導体

Outline of Final Research Achievements

In this project, we focused on carbocations, which are the most difficult carbon-active species to be controlled in organic synthesis, and developed new methods for their generation and stabilization. By designing an effective leaving group, we succeeded in developing a method for the generation of carbocation species by a unimolecular elimination mechanism under extremely mild conditions. In addition, we developed a capturing agent that reversibly coordinates to and stabilizes the generated cationic species, and the reactions with nucleophiles proceed after the capturing solution is stored for a certain period.

Free Research Field

化学系薬学

Academic Significance and Societal Importance of the Research Achievements

有機合成化学において、カルバニオン、ラジカル、カルベノイドなどが様々に用いられていることと比べて、同じ活性炭素反応種のカルボカチオンは特に制御が難しいため、その実用性は高いとは言い難い。本研究成果は、このカルボカチオンの発生と安定性を制御するための新たな方法論を提唱・確立する点で高い学術的意義があると同時に、これによりカルボカチオンの特長を活かした新たな活用が可能となり、医薬品開発をはじめ有機合成を基盤とする様々な研究や産業の発展を通した社会貢献が期待される。