Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

2013

Číslo periodika v rámci svazku

15

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

3158-3165

Kód UT WoS článku

000320173900023

EID výsledku v databázi Scopus

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