Magnesium-induced regiospecific C-silylation of suitably substituted enoates and dienoates

The beta-aryl-beta-silyl and beta,beta-disilyl propionates have been synthesized from cinnamates and beta-silyl acrylates by a regiospecific reductive C-silylation using Mg/silyl chloride/DMF system at room temperature. These reductive C-silylation conditions have also been applied to delta-aryl substituted dienoates wherein silylation took place at the delta-position leading to the synthesis of single regioisomeric allylsilanes with very high stereoselectivity. (C) 2010 Elsevier Ltd. All rights reserved.