Electrophilic amination of diorganozinc reagents by oxaziridines

Electrophilic amination of organozinc reagents by oxaziridines has been studied. Diorganozinc reagents R2Zn (R = alkyl or aryl) react with N-Boc oxaziridine to afford N-Boc protected primary amines BocNHR in moderate to good yields. No additives are needed in this reaction, which proceeds at 0 °C. We suggest that the presence of two heteroatoms in oxaziridine allows Lewis base activation of the diorganozinc reagent.