Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide.
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.
Concellón
J M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Bernad
P L
PL
Bardales
E
E