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Statements

Subject Item
n2:RIV%2F00216208%3A11160%2F13%3A10196556%21RIV14-GA0-11160___
rdf:type
n9:Vysledek skos:Concept
rdfs:seeAlso
http://pubs.rsc.org/en/content/articlehtml/2013/ra/c3ra43785j
dcterms:description
Chiral ionic liquids (CILs) tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate were investigated as chiral additives in the Pd-catalyzed enantioselective hydrogenation of alpha,beta-unsaturated ketones. These CILs were easily prepared in one step from the aminoacid and tetrabutylammonium hydroxide and characterized (NMR, IR, optical rotation, elemental analysis, DSC, viscosity, decomposition temperature). The research strategy was to assess the antimicrobial toxicity (>20 strains) and biodegradability (OECD 301D) of the CILs at the same time as undertaking the asymmetric catalysis study. The Pd-catalyzed enantioselective hydrogenation of the carbon-carbon double bond of alpha,beta-unsaturated ketones under mild conditions (room temperature, 1 atm of H-2) in different solvents with CILs present. The best results were obtained in i-PrOH after 18 hours of reaction with a i-PrOH/IL ratio of 5. While all three CILs have low antimicrobial toxicity to a wide range of bacteria and fungi, tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate did not pass the Closed Bottle biodegradation test. Chiral ionic liquids (CILs) tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate were investigated as chiral additives in the Pd-catalyzed enantioselective hydrogenation of alpha,beta-unsaturated ketones. These CILs were easily prepared in one step from the aminoacid and tetrabutylammonium hydroxide and characterized (NMR, IR, optical rotation, elemental analysis, DSC, viscosity, decomposition temperature). The research strategy was to assess the antimicrobial toxicity (>20 strains) and biodegradability (OECD 301D) of the CILs at the same time as undertaking the asymmetric catalysis study. The Pd-catalyzed enantioselective hydrogenation of the carbon-carbon double bond of alpha,beta-unsaturated ketones under mild conditions (room temperature, 1 atm of H-2) in different solvents with CILs present. The best results were obtained in i-PrOH after 18 hours of reaction with a i-PrOH/IL ratio of 5. While all three CILs have low antimicrobial toxicity to a wide range of bacteria and fungi, tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate did not pass the Closed Bottle biodegradation test.
dcterms:title
Tetrabutylammonium prolinate-based ionic liquids: a combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment Tetrabutylammonium prolinate-based ionic liquids: a combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment
skos:prefLabel
Tetrabutylammonium prolinate-based ionic liquids: a combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment Tetrabutylammonium prolinate-based ionic liquids: a combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment
skos:notation
RIV/00216208:11160/13:10196556!RIV14-GA0-11160___
n9:predkladatel
n10:orjk%3A11160
n3:aktivita
n14:P n14:I
n3:aktivity
I, P(GAP207/10/2048)
n3:cisloPeriodika
48
n3:dodaniDat
n7:2014
n3:domaciTvurceVysledku
n18:6556981
n3:druhVysledku
n17:J
n3:duvernostUdaju
n19:S
n3:entitaPredkladatele
n20:predkladatel
n3:idSjednocenehoVysledku
110741
n3:idVysledku
RIV/00216208:11160/13:10196556
n3:jazykVysledku
n13:eng
n3:klicovaSlova
amino-acids; chiral modifiers; kinetic resolution; conjugate reduction; Pd catalysts; enantioselective hydrogenation; functionalized side-chains; improved reductive properties; acid ethyl-ester; alpha,beta-unsaturated carbonyl-compounds
n3:klicoveSlovo
n4:chiral%20modifiers n4:acid%20ethyl-ester n4:conjugate%20reduction n4:functionalized%20side-chains n4:improved%20reductive%20properties n4:beta-unsaturated%20carbonyl-compounds n4:alpha n4:amino-acids n4:enantioselective%20hydrogenation n4:Pd%20catalysts n4:kinetic%20resolution
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[FA60967C9582]
n3:nazevZdroje
RSC Advances
n3:obor
n21:CC
n3:pocetDomacichTvurcuVysledku
1
n3:pocetTvurcuVysledku
11
n3:projekt
n8:GAP207%2F10%2F2048
n3:rokUplatneniVysledku
n7:2013
n3:svazekPeriodika
3
n3:tvurceVysledku
Ghavre, Mukund Haiss, Annette Bouquillon, Sandrine Gathergood, Nicholas Ferlin, Nadege Quilty, Brid Kuemmerer, Klaus Gatard, Sylvain Courty, Matthieu Nhien, Albert Nguyen Van Pour, Milan
n3:wos
000327261700102
s:issn
2046-2069
s:numberOfPages
11
n15:doi
10.1039/c3ra43785j
n5:organizacniJednotka
11160