Evaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives

• Jan Bartáček,
• Karel Chlumský,
• Jan Mrkvička,
• Lucie Paloušová,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2024, 20, 684–691, doi:10.3762/bjoc.20.62

• enhanced economic efficiency, eco-friendly practices, and reduced waste. Catalysts with the highest enantioselectivity have been employed in the synthesis of essential chiral intermediates for drug production, such as amprenavir [12], rivaroxaban [13][14], linezolid [13] and salmeterol [7]. Therefore

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• antibiotic linezolid (1) and the anticoagulant rivaroxaban (2) – belong among modern pharmaceutics, which contain an oxazolidine-2-one moiety bearing a stereogenic center. The chirality of these drugs is a fundamental attribute for their biological activity. Herein, one of the efficient asymmetric syntheses

• syntheses of these drugs were obtained in high yields and enantiomeric excesses of up to 91% ee. Keywords: asymmetric Henry reaction; enantioselective catalysis; linezolid; oxazolidine-2-one derivatives; rivaroxaban; Introduction Oxazolidine-2-one derivatives represent an important branch of

• pharmaceutical substances [1][2][3]. This class includes for instance oxazolidine-type antibiotics [3], e.g., linezolid (1) [4] (sold under the trade name Zyvox® (Figure 1) or tedizolid [5] (sold under the trade name Sivextro®), and the anticoagulant rivaroxaban (2) [6][7] (Figure 1), a member of DOACs (direct