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Synthesis 2009(15): 2646-2649  
DOI: 10.1055/s-0029-1216860
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Piperidinones through a Radical Cascade

Edouard Godineau, Yannick Landais*
University Bordeaux-1, UMR-CNRS 5255, 351 cours de la libération, 33405 Talence Cedex, France
Fax: +33(5)40006286; e-Mail: y.landais@ism.u-bordeaux1.fr;
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Publication History

Received 24 March 2009
Publication Date:
29 May 2009 (online)

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Abstract

Fused piperidinones were assembled from chiral allylsilanes possessing an oxime moiety using a stereocontrolled formal [2+2+2] radical-ionic process. The cascade involves the addition of an α-iodo ester to an ene oxime, which is then followed by a 5-exo-trig cyclization onto the aldoxime function producing an alkoxyaminyl radical species that finally lactamizes to afford piperidinones. Application of the radical cascade to ketoximes led instead to cyclopentanes incorporating two ester fragments as a result of a recombination process.

Key words

radical reactions - silicon - domino reactions - piperidines - cyclizations

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9

The term [2+2+2] refers here as a process involving 2 atoms + 2 atoms + 2 atoms and not to a concerted process.