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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.
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https://hal-polytechnique.archives-ouvertes.fr/hal-00966617
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Submitted on : Wednesday, March 26, 2014 - 9:52:03 PM
Last modification on : Thursday, March 5, 2020 - 6:26:55 PM

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CNRS | X | X-DCSO | INC-CNRS | X-DEP-CHIM

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Kelvin Kau Kiat Goh, Sunggak Kim, Samir Zard. A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (23), pp.12274-12279. ⟨10.1021/jo402169v⟩. ⟨hal-00966617⟩

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