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Synthesis 2011(13): 2085-2090  
DOI: 10.1055/s-0030-1260039
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© Georg Thieme Verlag Stuttgart ˙ New York

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

Vellaisamy Sridharan, Nikolay Vologdin, Marie-Alice Virolleaud, Damien Bonne, Cyril Bressy, Gaëlle Chouraqui, Laurent Commeiras, Jean-Luc Parrain, Yoann Coquerel, Jean Rodriguez*
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, iSm2 - UMR CNRS 6263, Centre Saint Jérôme, Service 531, 13397 Marseille Cedex 20, France
Fax: +33(4)91289187; e-Mail: jean.rodriguez@univ-cezanne.fr;
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Publication History

Received 24 February 2011
Publication Date:
11 May 2011 (online)

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Abstract

An efficient synthesis 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.

Key words

sulfoximine - 5,5-spiroketals - consecutive reaction - chalcogran

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