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A Novel Amination Reaction with Diphenyl Phosphorazidate: Synthesis of α‐amino‐acid derivatives
Author(s) -
Villalgordo José M.,
Linden Anthony,
Heimgartner Heinz
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790122
Subject(s) - chemistry , electrophilic amination , amination , reagent , electrophile , organic chemistry , amino acid , acid anhydride , reaction conditions , medicinal chemistry , combinatorial chemistry , catalysis , biochemistry , epoxy
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 .