A Novel Amination Reaction with Diphenyl Phosphorazidate: Synthesis of α‐amino‐acid derivatives | Zendy

Villalgordo José M. | Zendy; Linden Anthony | Zendy; Heimgartner Heinz | Zendy

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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 .

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