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Synfacts 2006(1): 0030-0030  
DOI: 10.1055/s-2005-921692
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Dihydropyridinones and Hexahydroindolizin-7(1H)-one Derivatives

Contributor(s): Victor Snieckus, Till Vogel
M. Dziedzic, G. Lipner, J. M. Illangua, B. Furman*
Polish Academy of Science, Warsaw, Poland and Universidad de Sevilla, Spain
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

The propargylsilane dihydropyridinones, prepared in a ytterbium(III) triflate-catalyzed three-component reaction involving an aza-Diels-Alder reaction with Danishefsky’s diene, undergoes a fluoride-induced intramolecular Michael addition to afford allenidene indolizidinones in good to excellent yields as single diastereomers. The ste­reochemistry was established by NMR and X-ray crystal structure analysis. An extension to the preparation of analogous aza[4.4.0]bicyclic systems is also reported.