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

Kelvin Kau Kiat Goh (1, 2) , Sunggak Kim (2) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique
2 Nanyang Technological University [Singapour]

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.

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