N-Boc-Oxaziridines as NH₂ ⁺ Synthons for Electrophilic Amination

Significance

As shown in this work, diorgano­zinc reagents react with N-Boc-oxaziridines to afford Boc-protected primary amines in moderate to good yields. The reaction proceeds at 0 ˚C and does not require the use of any additive. A plausible reaction mechanism is presented presuming the transfer of the zinc organyl residue to nitrogen with subsequent formation of a zinc amide. Aqueous work-up then yields the protected primary amine.