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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.
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.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | English |
| Date: | 1996 |
| Deposited On: | 25 Nov 2013 08:26 |
| Last Modified: | 10 Mar 2025 02:38 |
| Publisher: | Wiley-Blackwell |
| ISSN: | 0018-019X |
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Prof. Hans E. Schmid-Stiftung |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1002/hlca.19960790122 |
| Project Information: |
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Villalgordo, Jose M