Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33147692" target="_blank" >RIV/61989592:15310/13:33147692 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201300093" target="_blank" >http://dx.doi.org/10.1002/ejoc.201300093</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201300093" target="_blank" >10.1002/ejoc.201300093</a>
Alternative languages
Result language
angličtina
Original language name
Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes
Original language 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-mediatedcleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2013
Issue of the periodical within the volume
15
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
3158-3165
UT code for WoS article
000320173900023
EID of the result in the Scopus database
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