An Asymmetric Organocatalytic One-Pot Strategy to Octahydroacridines

An elegant sequence: An efficient method for the formation of octahydroacridines provides high yields and a high level of stereogenic control, and displays great tolerance towards different aldehydes, anilines, and nucleophiles (see scheme; TMS=trimethylsilyl; EWG=electron‐withdrawing group). The us...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-02, Vol.50 (7), p.1580-1583
Hauptverfasser: Dickmeiss, Gustav, Jensen, Kim L., Worgull, Dennis, Franke, Patrick T., Jørgensen, Karl Anker
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Sprache:eng
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Zusammenfassung:An elegant sequence: An efficient method for the formation of octahydroacridines provides high yields and a high level of stereogenic control, and displays great tolerance towards different aldehydes, anilines, and nucleophiles (see scheme; TMS=trimethylsilyl; EWG=electron‐withdrawing group). The use of different nucleophiles verifies an endo transition state in which π–π overlap of the aromatic rings plays an important role in the reactivity and selectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006608