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Article Dans Une Revue European Journal of Organic Chemistry Année : 2006

An expedient route to new spiroheterocycles: synthesis and structural studies.

Résumé

We have developed a short, efficient and enantioselective synthesis of 1,4,7,10-tetraoxa- and 1,7-dioxa-4,10-dithiaspiro[5.5]undecanes. The method involved the reaction of solketal 5 or thiol derivative 6 with 1,3-dichloropropanone O-benzyloxime (4) which affords the conveniently protected symmetrical ketones 7 and 8. Elaboration of the required 4,10-disubstituted-1,7-dioxaspiro[5.5]undecane systems 1 and 2 entailed a final one-pot deprotection-spirocyclization process in an acidic medium. The structures and configurations of the spiroketals were established unambiguously by NMR spectroscopy

Domaines

Chimie organique
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Dates et versions

hal-00119575 , version 1 (27-02-2007)

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Marlène Goubert, Isabelle Canet, Marie-Eve Sinibaldi. An expedient route to new spiroheterocycles: synthesis and structural studies.. European Journal of Organic Chemistry, 2006, pp.4805-4812. ⟨10.1002/ejoc.200600448⟩. ⟨hal-00119575⟩
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