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Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide
J M Concellón1, P L Bernad, E Bardales
1Departamento de Química Orgánica e Inorgánica, Facultad de Química Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Organic Letters
|March 27, 2001
Abstract:
beta-Elimination of O-acetyl 1-chloro-1-trimethylsilylalkan-2-ols 1 was achieved by using samarium diiodide as a metaling reagent and afforded the corresponding (Z)-vinylsilanes with high stereoselectivity. The starting compounds 1 were easily prepared by treatment of different aldehydes with (chlorolithiomethyl)trimethylsilane and further acetylation.