A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

Kelvin Kau Kiat Goh; Sunggak Kim; Samir Zard

doi:10.1021/jo402169v

A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

Kelvin Kau Kiat Goh ^{1, 2} Sunggak Kim ² Samir Zard ¹

1 DCSO - Laboratoire de synthèse organique

2 Division of Chemistry and Biological Chemistry

Abstract : An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

Type de document :

Article dans une revue

Journal of Organic Chemistry, American Chemical Society, 2013, 78 (23), pp.12274-12279. 〈10.1021/jo402169v〉

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https://hal-polytechnique.archives-ouvertes.fr/hal-00966617
Contributeur : Denis Roura <>
Soumis le : mercredi 26 mars 2014 - 21:52:03
Dernière modification le : jeudi 10 mai 2018 - 02:07:52

A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

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A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

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