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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F13%3A33147692%21RIV14-GA0-15310___
rdf:type
skos:Concept n12:Vysledek
dcterms:description
We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid. We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid.
dcterms:title
Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
skos:prefLabel
Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
skos:notation
RIV/61989592:15310/13:33147692!RIV14-GA0-15310___
n12:predkladatel
n13:orjk%3A15310
n5:aktivita
n15:P
n5:aktivity
P(EE2.3.20.0009), P(GAP207/12/0473), P(ME09057)
n5:cisloPeriodika
15
n5:dodaniDat
n14:2014
n5:domaciTvurceVysledku
n6:4422759 n6:3227413
n5:druhVysledku
n16:J
n5:duvernostUdaju
n19:S
n5:entitaPredkladatele
n7:predkladatel
n5:idSjednocenehoVysledku
97092
n5:idVysledku
RIV/61989592:15310/13:33147692
n5:jazykVysledku
n11:eng
n5:klicovaSlova
Bicyclic compounds; Solid-phase synthesis; Nucleophilic addition; Heterocycles; Peptidomimetics
n5:klicoveSlovo
n8:Heterocycles n8:Nucleophilic%20addition n8:Peptidomimetics n8:Bicyclic%20compounds n8:Solid-phase%20synthesis
n5:kodStatuVydavatele
DE - Spolková republika Německo
n5:kontrolniKodProRIV
[E3691D894F27]
n5:nazevZdroje
European Journal of Organic Chemistry
n5:obor
n9:CC
n5:pocetDomacichTvurcuVysledku
2
n5:pocetTvurcuVysledku
4
n5:projekt
n17:EE2.3.20.0009 n17:ME09057 n17:GAP207%2F12%2F0473
n5:rokUplatneniVysledku
n14:2013
n5:svazekPeriodika
2013
n5:tvurceVysledku
Zajíček, Jaroslav Oliver, Allen G Schütznerová, Eva Krchňák, Viktor
n5:wos
000320173900023
s:issn
1434-193X
s:numberOfPages
8
n20:doi
10.1002/ejoc.201300093
n18:organizacniJednotka
15310