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- Title
Enantioselective Michael Addition of the 2-(1-Ethylpropoxy)acetaldehyde to N-[(1 Z)-2-Nitroethenyl]acetamide - Optimization of the Key Step in the Organocatalytic Oseltamivir Synthesis.
- Authors
Hajzer, Viktória; Latika, Attila; Durmis, Július; Šebesta, Radovan
- Abstract
Organocatalytic Michael addition of alkoxyacetaldehyde 1 to N-protected 2-nitroethene-1-amine 2 ( Scheme 2) is a key step in the synthesis of an important antiviral agent, oseltamivir. Screening of a large array of structurally diverse acids as potential promoters led to the identification of several useful acidic additives for this reaction ( Tables 1-4). Also other reaction parameters were investigated with the aim of improving the diastereoselectivity of the Michael addition, while maintaining high enantiomer purity and yield ( Tables 5 and 6).
- Subjects
ACETALDEHYDE; ACETAMIDE; ENANTIOSELECTIVE catalysis; OSELTAMIVIR; CHEMICAL synthesis; MICHAEL reaction
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 12, p2421
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200527