Please use this identifier to cite or link to this item: http://dx.doi.org/10.18419/opus-6975
Authors: Laschat, Sabine
Lauterwein, Jürgen
Title: Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives
Issue Date: 1993
metadata.ubs.publikation.typ: Zeitschriftenartikel
metadata.ubs.publikation.source: 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
Abstract: 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.
Appears in Collections:15 Fakultätsübergreifend / Sonstige Einrichtung

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