Mandelate and prolinate ionic liquids: synthesis, characterization, catalytic and biological activity

Autor:	Zbigniew Dąbrowski, Tadeusz Praczyk, Jacek Cybulski, Katarzyna Materna, Juliusz Pernak, Alicja Michalczyk, Anna Wiśniewska, Filip Walkiewicz, Anna Kulig-Adamiak
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Ketone Organic Chemistry Enantioselective synthesis Cyclohexanone Biochemistry Chemical synthesis chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Ionic liquid Michael reaction Organic chemistry Enantiomeric excess
Zdroj:	Tetrahedron Letters. 52:1325-1328
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2011.01.069
Popis:	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 CH 2 Cl 2 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fe631a97ad0894f14170afd6306550d7 https://doi.org/10.1016/j.tetlet.2011.01.069 Zobrazit plný text záznamu Full Text from ScienceDirect