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Statements

Subject Item
n2:RIV%2F00216275%3A25310%2F08%3A00007557%21RIV09-GA0-25310___
rdf:type
skos:Concept n19:Vysledek
dcterms:description
Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding 1a, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24?72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17. Dvě třídy derivátů terpenů (diketony a monoximy) byly kondenzovány na deriváty imidazolu s využitím dvou metod. Metoda A zahrnuje kondenzaci diketonů s aldehydy, metoda B pak reakci monoximů s aminy. Mechanismus metody je rovněž diskutován. Celkem bylo syntetizováno a charakterizováno 11 nových derivátů imidazolu. Dva intermediáty/vedlejší produkty byly rovněž charakterizovány pomoci X-ray analýzy. Syntetizované ligandy byly aplikovány v asymetrické Henryho reakci, kdy bylo dosaženo reakčních časů 24-72 h a enantioselektivit do 32%. Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding 1a, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24?72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17.
dcterms:title
Využití terpenových derivátů v syntéze terpen-imidazolů s aplikací v nitroaldolové reakci Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction
skos:prefLabel
Využití terpenových derivátů v syntéze terpen-imidazolů s aplikací v nitroaldolové reakci Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction
skos:notation
RIV/00216275:25310/08:00007557!RIV09-GA0-25310___
n4:aktivita
n5:Z n5:P
n4:aktivity
P(GP203/07/P013), Z(MSM0021627501)
n4:cisloPeriodika
21
n4:dodaniDat
n18:2009
n4:domaciTvurceVysledku
n12:1821199 n12:9403361
n4:druhVysledku
n16:J
n4:duvernostUdaju
n8:S
n4:entitaPredkladatele
n11:predkladatel
n4:idSjednocenehoVysledku
402012
n4:idVysledku
RIV/00216275:25310/08:00007557
n4:jazykVysledku
n17:eng
n4:klicovaSlova
imidazole; terpenes; asymmetric catalysis
n4:klicoveSlovo
n10:terpenes n10:imidazole n10:asymmetric%20catalysis
n4:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n4:kontrolniKodProRIV
[2C7ABD738AB1]
n4:nazevZdroje
Tetrahedron:Asymmetry
n4:obor
n14:CC
n4:pocetDomacichTvurcuVysledku
2
n4:pocetTvurcuVysledku
4
n4:projekt
n15:GP203%2F07%2FP013
n4:rokUplatneniVysledku
n18:2008
n4:svazekPeriodika
19
n4:tvurceVysledku
Bureš, Filip Šimon, Petr Kulhánek, Jiří Schweizer, Bernd
n4:zamer
n13:MSM0021627501
s:issn
0957-4166
s:numberOfPages
8
n6:organizacniJednotka
25310