Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines

A synthesis of methyl (2S)-2-amino-4-oxo-2,4-diphenylbutanoate has been achieved via a novel one-pot non-transition metal mediated deprotection of the N-allyloxycarbonyl amine using iodine in wet acetonitrile. The applicability of this transformation has been demonstrated by deprotecting a variety of N-allyloxycarbonyl amines, α-aminomethyl esters and simple N-allyloxycarbonyl alkyl amines. Deprotection occurs in high yield (82–93%) without erosion of the optical purity of the chiral substrates.