The asymmetric Henry reaction as synthetic tool for production of drugs Linezolid and Rivaroxaban

  1. Martin Vrbický,
  2. Karel Macek,
  3. Jaroslav Pochobradský,
  4. Jan SvobodaORCID Logo,
  5. Miloš SedlákORCID Logo and
  6. Pavel DrabinaORCID Logo

Submitting author affiliation: University of Pardubice, Pardubice, Czech Republic

Beilstein Arch. 2022, 20224. https://doi.org/10.3762/bxiv.2022.4.v1

Published 17 Jan 2022

  • Preprint

Abstract

The human drugs – antibiotic Linezolid (1) and anticoagulant Rivaroxaban (2) – belongs among modern pharmaceutics, which contain oxazolidine-2-one moiety bearing stereogenic centre. The chirality of these drugs is fundamental attribute of their biological activity. Herein, one of the efficient asymmetric syntheses of those drugs was studied in detail. High enantioselective catalysts were tested in the key step of the synthetic procedure, i.e. asymmetric Henry reaction, under different reaction conditions, using several starting aldehydes. The corresponding nitroaldols as chiral intermediates of those drugs were obtained in high yields and enantiomeric excess up to 91% ee.

Keywords: Asymmetric Henry reaction; Enantioselective catalysis; Linezolid; Oxazolidine-2-one derivatives; Rivaroxaban

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Vrbický, M.; Macek, K.; Pochobradský, J.; Svoboda, J.; Sedlák, M.; Drabina, P. Beilstein Arch. 2022, 20224. doi:10.3762/bxiv.2022.4.v1

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