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Synfacts 2011(8): 0835-0835  
DOI: 10.1055/s-0030-1260855
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Ruthenium-Catalyzed Synthesis of Complex Indolizidinones

Contributor(s): Victor Snieckus, Emilie David
E. Ascic, J. F. Jensen, T. E. Nielsen*
Technical University of Denmark, Lyngby, Denmark
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

Inspired by previous work concerning the synthesis of six- and seven-membered unsaturated lactams (S. Fustero et al. J. Org. Chem. 2006, 71, 2706; A. Mallagaray, G. Domínguez, A. Gradillas, J. Pérez-Castells Org. Lett. 2008, 10, 597) using a ring-closing metathesis (RCM)-isomerization sequence, enamides 1 were shown to undergo isomerization-cyclization via reactive N-acyliminium intermediates 2. The presence of a tethered nucleophile causes cyclization to afford indolizidinones 3 under ruthenium-catalyzed (A) conditions.