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Authors: Laschat, Sabine
Lauterwein, Jürgen
Title: Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives
Issue Date: 1993 Zeitschriftenartikel Journal of Organic Chemistry 58 (1993), S. 2856-2861. URL
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.
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