Mandelate and prolinate ionic liquids: synthesis, characterization, catalytic and biological activity |
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Authors: | Jacek CybulskiAnna Wi?niewska Anna Kulig-AdamiakZbigniew D?browski Tadeusz PraczykAlicja Michalczyk Filip WalkiewiczKatarzyna Materna Juliusz Pernak |
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Affiliation: | a Industrial Chemistry Research Institute, ul. Rydygiera 8, 01-793 Warsaw, Poland b Institute of Plant Protection, ul. W. Wegorka 20, 60-318 Poznan, Poland c The Institute of Industrial Organic Chemistry, ul. Annopol 6, 03-236 Warsaw, Poland d Poznan University of Technology, Faculty of Chemical Technology, pl. M. Sklodowskiej-Curie 2, 60-965 Poznan, Poland |
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Abstract: | A group of quaternary ammonium mandelates and l-prolinates, as ionic liquids, were synthesized and characterized. The prepared salts were soluble in water and showed high surface activity. The described synthesis of l-prolinate was simple and the obtained ionic liquid contained a chiral anion. l-Prolinate in CH2Cl2 was employed for the asymmetric Michael addition of a ketone to nitrostyrene. A yield of 60%, enantioselectivity (upto 50% ee), and good diastereoselectivity (syn/anti ratio of up to 90:10) were obtained for the asymmetric addition of cyclohexanone. These novel ionic liquids proved to be very effective anti-microbial and anti-fungal agents, especially didecyldimethylammonium l-prolinate. Additionally, it was found that phytotoxicity can be a useful tool in assessing the optical forms of ionic liquids. |
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Keywords: | Ionic liquids Mandelates Prolinates Biological activity Catalysis Phytotoxicity |
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