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A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives


Villalgordo, Jose M; Linden, Anthony; Heimgartner, Heinz (1996). A novel amination reaction with Diphenyl Phosphorazidate: Synthesis of alpha-Amino-Acid Derivatives. Helvetica Chimica Acta, 79(1):213-219.

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1996
Deposited On:25 Nov 2013 08:26
Last Modified:05 Apr 2016 17:11
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Prof. Hans E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.1002/hlca.19960790122

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