The reaction of enolates of α‐unsubstituted carboxamides 3 with diphenyl phosphorazidate (DPPA) and di(tert‐butyl) dicarbonate (‘Boc anhydride’) in THF at −78° yielded 2‐{[(tert‐butoxy)carbonyl]amino}carboxamides 5 (Scheme 2) which are derivatives of α‐amino acids. In this reaction, DPPA acts as an electrophilic amination reagent. A reaction mechanism is proposed in Scheme 3.
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Villalgordo et al. (1996) studied this question.
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