Electrophilic Thiocyanato Reagent Assisted Oxa-Michael/Thiocyanation of α,β-Unsaturated Ketones

A route for thiocyanation-functionalization of the electron-deficient C═C double bond was developed. Regioselective thiocyanation-etherification of α,β-unsaturated ketones was achieved. The desired products were obtained in moderate to high yields under mild conditions. It was suggested that the nucleophile was activated by the electrophilic thiocyanato reagent, and difunctionalization was achieved through a 1,4-addition/thiocyanation pathway.