Rhodium(III)-Catalyzed Synthesis of Spiropiperidine Derivatives via C–H Activation

Spiropiperidine derivatives, an important class of bioactive molecules, were synthesized under mild conditions by rhodium­(III)-catalyzed intramolecular ArC–H activation. This reaction provides a novel route to highly substituted tricyclic spiropiperidines in good to excellent yields. Under acidic c...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (4), p.2324-2340
Main Authors: Peneau, Augustin, Retailleau, Pascal, Guillou, Catherine, Chabaud, Laurent
Format: Article
Language:English
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Summary:Spiropiperidine derivatives, an important class of bioactive molecules, were synthesized under mild conditions by rhodium­(III)-catalyzed intramolecular ArC–H activation. This reaction provides a novel route to highly substituted tricyclic spiropiperidines in good to excellent yields. Under acidic conditions the resulting enamines reacted with pendant amides to afford spiropiperidines derivatives possessing an original tetracyclic structure.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b03252