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

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Abstract

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.

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Acknowledgments

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

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Authors and Affiliations

  1. Synkola Ltd., Mlynská Dolina, 84215, Bratislava, Slovakia

    Viktória Hajzer, Attila Latika & Július Durmis

  2. Department of Plastics and Rubber, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, 81237, Bratislava, Slovakia

    Pavel Alexy

  3. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina CH-2, 84215, Bratislava, Slovakia

    Radovan Šebesta

Authors
  1. Viktória Hajzer
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  2. Pavel Alexy
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  3. Attila Latika
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  4. Július Durmis
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  5. Radovan Šebesta
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Corresponding author

Correspondence to Radovan Šebesta.

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Hajzer, V., Alexy, P., Latika, A. et al. Optimization of stereoselective Michael addition of 2-(pentan-3-yloxy)acetaldehyde to N-[(Z)-2-nitroethenyl]acetamide with the aid of design of experiments. Monatsh Chem 146, 1541–1545 (2015). https://doi.org/10.1007/s00706-015-1486-8

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  • DOI: https://doi.org/10.1007/s00706-015-1486-8

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