Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 9, pp 1541–1545 | Cite as

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

  • Viktória Hajzer
  • Pavel Alexy
  • Attila Latika
  • Július Durmis
  • Radovan ŠebestaEmail author
Original Paper


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


Organocatalysis Michael addition Oseltamivir Design of experiment Alkyloxyacetaldehyde Nitroalkene 



This work was supported by Slovak Research and Development Agency, grant no. APVV-0067-11.

Supplementary material

706_2015_1486_MOESM1_ESM.docx (495 kb)
Supplementary material 1 (DOCX 495 kb)


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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  1. 1.Synkola Ltd.BratislavaSlovakia
  2. 2.Department of Plastics and Rubber, Faculty of Chemical and Food TechnologySlovak Technical UniversityBratislavaSlovakia
  3. 3.Department of Organic Chemistry, Faculty of Natural SciencesComenius University in BratislavaBratislavaSlovakia

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