A series of N-alkyl-2-oxoalkanesulfonamides have been synthesized by reacting silyl enol ethers with N-alkyl-sulfamoyl chlorides. Their reactivity towards electrophiles was investigated in order to explore the regio-aand stereoselectivity of the process. 2- Oxoalkanesulfonamides were used to prepare 5-(methylsulfamoyl)-1, 4-dihydropyridines derivatives.