Synthesis of unnatural selenocystines and β-aminodiselenides via regioselective ring-opening of sulfamidates using a sequential, one-pot, multistep strategy

A variety of N-alkyl-&#946;-aminodiselenides have been synthesized in high yield from sulfamidates under mild reaction conditions using potassium selenocyanate and benzyltriethylammonium tetrathiomolybdate ([BnNEt<SUB>3</SUB>]<SUB>2</SUB>MoS<SUB>4</SUB>) in a sequential, one-pot, multistep reaction. The tolerance of multifarious protecting groups under the reaction conditions is discussed. The methodology was successfully extended to the synthesis of selenocystine, 3,3'-dialkylselenocystine, and 3,3'-diphenylisoselenocystine and their direct incorporation into peptides