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http://dx.doi.org/10.18419/opus-6975
Autor(en): | Laschat, Sabine Lauterwein, Jürgen |
Titel: | Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives |
Erscheinungsdatum: | 1993 |
Dokumentart: | Zeitschriftenartikel |
Erschienen in: | Journal of Organic Chemistry 58 (1993), S. 2856-2861. URL http://dx.doi.org./10.1021/jo00062a033 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-41411 http://elib.uni-stuttgart.de/handle/11682/6992 http://dx.doi.org/10.18419/opus-6975 |
Zusammenfassung: | A new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,-4a,9,9a,l0-octahydroacridined erivatives 6. Both reactivity and cis/ trans selectivity of 6 were mainly dependent on the substitution pattern in the 3-position of the cyclization precursor 5. The type of Lewis acid plays only a minor role in determination of the cis/trans ratio. The synthetic utility of this new cyclization was increased by performing it as a one-pot reaction. Both absolute configuration and preferred conformation were assigned by detailed NMR studies. |
Enthalten in den Sammlungen: | 15 Fakultätsübergreifend / Sonstige Einrichtung |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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las5.pdf | 704,14 kB | Adobe PDF | Öffnen/Anzeigen |
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