Optimization of stereoselective Michael addition of 2-(pentan-3-yloxy)acetaldehyde to N-[(Z)-2-nitroethenyl]acetamide with the aid of design of experiments

Optimization of stereoselective Michael addition of 2-(pentan-3-yloxy)acetaldehyde to N-[(Z)-2-nitroethenyl]acetamide with the aid of design of experiments

Stereoselective Michael addition of 2-(pentan-3-yloxy)acetaldehyde to N -[( Z )-2-nitroethenyl]acetamide is a key step in the organocatalytic synthesis of oseltamivir, active ingredient in the anti-influenza drug Tamiflu. Several important reaction parameters were analyzed by the help of design of e...

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Veröffentlicht in:Monatshefte für Chemie 2015-09, Vol.146 (9), p.1541-1545
Hauptverfasser: Hajzer, Viktória, Alexy, Pavel, Latika, Attila, Durmis, Július, Šebesta, Radovan
Format: Artikel
Sprache:eng
Schlagworte:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Zusammenfassung:Stereoselective Michael addition of 2-(pentan-3-yloxy)acetaldehyde to N -[( Z )-2-nitroethenyl]acetamide is a key step in the organocatalytic synthesis of oseltamivir, active ingredient in the anti-influenza drug Tamiflu. Several important reaction parameters were analyzed by the help of design of experiments and optimum reaction conditions were found. These conditions led to improvements of the reaction outcomes. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-015-1486-8