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Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes

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Abstract

Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes, Michael adducts were obtained in high yields and with medium-to-high diastereo- (up to 13:1 d.r.) and enantiomeric purities (up to 99% ee). The reaction was less stereoselective with cyclic ketones than with aldehydes.

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Acknowledgements

This work was supported by the Slovak Research and Development Agency under the contract no. APVV-15-0039.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15, Bratislava, Slovakia

    Viera Poláčková, Patrícia Čmelová & Radovan Šebesta

  2. Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15, Bratislava, Slovakia

    Renáta Górová

Authors
  1. Viera Poláčková
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  2. Patrícia Čmelová
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  3. Renáta Górová
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  4. Radovan Šebesta
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Corresponding author

Correspondence to Radovan Šebesta.

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Poláčková, V., Čmelová, P., Górová, R. et al. Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes. Monatsh Chem 149, 729–736 (2018). https://doi.org/10.1007/s00706-017-2126-2

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  • DOI: https://doi.org/10.1007/s00706-017-2126-2

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