Perfluorinated Bis(dihydrooxazole) Complexes Immobilized on Fluorous Reversed-Phase Silica Gel as Recyclable Catalysts for EnantioselectiveDielsAlderReactions

Autor:	Willi Bannwarth, Eva M. Hensle
Rok vydání:	2012
Předmět:	Chemistry Silica gel Organic Chemistry Enantioselective synthesis chemistry.chemical_element Biochemistry Copper Catalysis Inorganic Chemistry chemistry.chemical_compound Drug Discovery Organic chemistry Leaching (metallurgy) Physical and Theoretical Chemistry Enantiomer Diels–Alder reaction
Zdroj:	Helvetica Chimica Acta. 95:2072-2083
ISSN:	0018-019X
DOI:	10.1002/hlca.201200380
Popis:	The three different perfluoroalkyl-tagged bis(dihydrooxazole)copper complexes 19–21 were synthesized and immobilized noncovalently on fluorous reversed-phase silica gel (FRPSG) by fluorousfluorous interactions (Schemes 2 and 3). These supported catalysts were successfully applied to asymmetric DielsAlder reactions in H2O and in CH2Cl2 (Scheme 4). Besides high conversion of the dienophile, we observed enantiomer excesses of up to 88% in H2O and 97% in CH2Cl2, and we were able to recover and re-use these catalytic systems several times. Despite the relatively high catalyst loading, the leaching of copper was remarkably low ranging from 2.4 to 5.9 ppm.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c4e45020913f6e95a96f692fe2ff5d35 https://doi.org/10.1002/hlca.201200380 Zobrazit plný text záznamu Plný text ve formátu PDF