Unusually High Reactivity of the C-Si Bond in the Lewis Acid Mediated Reactions of (E)-1-(Trimethylsilyl)-2-(isopropylthio)ethylene with Carbonyl Electrophiles

Abstract
In the reaction with benzaldehyde and with cyclic α,β-unsaturated ketones in the presence of Lewis acids (E)-1-(trimethylsilyl)-2-(isopropylthio)ethylene exhibits enhanced reactivity compared to that of (E)-1-(trimethylsilyl)-hept-1-ene. Moreover depending upon the nature of the Lewis acid used, stoichiometric or catalytic pathways can be envisioned which lead to different reaction products.

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