Abstract The reactions of 1-(trimethylsiloxy)-3-methylcyclopent-1-ene, 1-(trimethylsiloxy)-3- methylcyclohex-1-ene and 1-(trimethylsiloxy)-3, 3-dimethylcyclohex-1-ene with various alkylating agents in the presence of silver trifluoroacetate produced the corresponding 2, 3- dialkylated and 2, 3, 3-trialkylated cyclanones with high regiodifferentiation and stereoselection.