Stereospecific synthesis of 2,3-disubstituted aziridines from β-alkylamino phenylselenides

Reduction of α-phenylselanyl imines derived from β-phenylselanyl α-oxoesters or PhSeCl assisted nucleophilic addition of primary amines to α,β-unsaturated esters have led to β-alkylamino phenylselenides 4, 5, 12 and 13 which were cyclised into aziridines 8, 9 and 14 after selenium activation. threo-Amino selenides led stereospecifically to cis-2,3-disubstituted aziridines. Depending on the structure, non-functionalised amino selenides 19–20 were also cyclised into aziridines 21–22.