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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F10%3A00351445%21RIV11-MSM-61388963
rdf:type
n15:Vysledek skos:Concept
dcterms:description
Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction. Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction.
dcterms:title
Model synthesis of six-membered carbocyclic spironucleosides Model synthesis of six-membered carbocyclic spironucleosides
skos:prefLabel
Model synthesis of six-membered carbocyclic spironucleosides Model synthesis of six-membered carbocyclic spironucleosides
skos:notation
RIV/61388963:_____/10:00351445!RIV11-MSM-61388963
n3:aktivita
n4:Z n4:P
n3:aktivity
P(1M0508), Z(AV0Z40550506)
n3:cisloPeriodika
12
n3:dodaniDat
n5:2011
n3:domaciTvurceVysledku
n8:5104998 n8:1570889 n8:2131447
n3:druhVysledku
n18:J
n3:duvernostUdaju
n9:S
n3:entitaPredkladatele
n14:predkladatel
n3:idSjednocenehoVysledku
271830
n3:idVysledku
RIV/61388963:_____/10:00351445
n3:jazykVysledku
n17:eng
n3:klicovaSlova
spironucleosides; carbocyclic; Bucherer-Bergs reaction; Michaels addition; tandem reaction
n3:klicoveSlovo
n7:Bucherer-Bergs%20reaction n7:Michaels%20addition n7:tandem%20reaction n7:carbocyclic n7:spironucleosides
n3:kodStatuVydavatele
CZ - Česká republika
n3:kontrolniKodProRIV
[F6B4240810EA]
n3:nazevZdroje
Collection of Czechoslovak Chemical Communications
n3:obor
n13:CC
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
3
n3:projekt
n11:1M0508
n3:rokUplatneniVysledku
n5:2010
n3:svazekPeriodika
75
n3:tvurceVysledku
Hřebabecký, Hubert Dračínský, Martin Nencka, Radim
n3:wos
000285770100004
n3:zamer
n16:AV0Z40550506
s:issn
0010-0765
s:numberOfPages
14