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Consecutive Reactions with Sulfoximines: Straightforward Synthesis of Substituted 5,5-Spiroketals

Vellaisamy Sridharan 1 Nikolay Vologdin 1 Marie-Alice Virolleaud 1 Cyril Bressy 1 Gaëlle Chouraqui 1 Laurent Commeiras 1 Jean-Luc Parrain 1 Damien Bonne 1 Yoann Coquerel 1 Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : An efficient sysnthesis of 5,5-spiroketals, i.e. 1,6-dioxaspiro[4.4]nonane derivatives, is described from 2-(sulfonimidoylmethylene)tetrahydrofurans involving a consecutive epoxide opening / oxa-Michael spiroketalization sequence. This methodology was applied to the very direct synthesis of chalcogran, a beetle pheromone.
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Submitted on : Friday, March 9, 2012 - 9:17:34 AM
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Vellaisamy Sridharan, Nikolay Vologdin, Marie-Alice Virolleaud, Cyril Bressy, Gaëlle Chouraqui, et al.. Consecutive Reactions with Sulfoximines: Straightforward Synthesis of Substituted 5,5-Spiroketals. SYNTHESIS, Georg Thieme Verlag, 2011, pp.2085-2090. ⟨10.1055/s-0030-1260039⟩. ⟨hal-00677638⟩

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