Novel strategy for dynamic kinetic resolution by Pickering emulsion

2023 Fiscal Year Final Research Report

• Project/Area Number: 22K14681
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Osaka University
• Principal Investigator: Kanomata Kyohei 大阪大学, 大学院薬学研究科, 助教 (30880447)
• Project Period (FY): 2022-04-01 – 2024-03-31
• Keywords: ピッカリングエマルション / Pickeringエマルション / 酵素 / リパーゼ / 不斉合成

Outline of Final Research Achievements

Multi-component catalytic reactions in Pickering emulsion were developed. Especially, remarkable results were obtained in the dynamic kinetic resolution of alcohols. Lipase and aqueous sulfuric acid solution, which are inherently incompatible, successfully catalyzed the reaction in a single vessel by compartmentalizing the reaction media by a Pickering emulsion. Optically active esters were obtained in high yield and high optical purity from a wide range of racemic alcohols. The method was also applicable to tertiary alcohols, which are considered challenging task in synthetic organic chemistry. The tertiary alcohols are impossible to racemize by the conventional redox mechanism, and the results show the usefulness of the present method using aqueous sulfuric acid in Pickering emulsions.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究は、食品・化粧品業界で開発が進んでいるPickeringエマルションを有機合成化学における反応場の分離に転用した異分野融合研究である。光学活性エステルは多くの生物活性物質の重要な基本骨格であり、その供給技術は、医農薬など精密化成品の創出・生産に不可欠である。この要請に対し本成果は、Pickeringエマルションを用いる独自技術によって、操作性・安全性・大スケールへの拡張性を兼ね備えた実践性の高い手法を提供するものである。