Publication: A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives
A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives
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Villalgordo, J. M., Linden, A., & Heimgartner, H. (1996). A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives. Helvetica Chimica Acta, 79(1), 213–219. https://doi.org/10.1002/hlca.19960790122
Abstract
Abstract
Abstract
The reaction of enolates of alpha-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 alpha-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, Jose M
- Heimgartner, Heinz
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Citations
Villalgordo, J. M., Linden, A., & Heimgartner, H. (1996). A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives. Helvetica Chimica Acta, 79(1), 213–219. https://doi.org/10.1002/hlca.19960790122
