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A Novel Amination Reaction with Diphenyl Phosphorazidate: Synthesis of α-amino-acid derivatives

✍ Scribed by José M. Villalgordo; Anthony Linden; Heinz Heimgartner

Publisher: John Wiley and Sons
Year: 1996
Tongue: German
Weight: 333 KB
Volume: 79
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19960790122

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✦ Synopsis

Abstract

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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