Peroxodisulfate-assisted synthesis of 2-thiocyanato glycals and their transformation to C-2-thio acrylo/aryl nitrile-substituted glycals.

Abstract

An efficient regioselective method to attach thiocyanato groups at the β-position of enol double bonds in sugar enol ethers using KSCN and potassium persulfate has been developed. The highly regioselective addition of the resulting sugar thiocyanate to electron rich species like terminal alkynes and benzynes under Pd catalysis generated C-2-thio acrylo/aryl nitrile glycals via simultaneous introduction of thio and cyano groups into carbon-carbon triple bonds.