The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban
The human drugs – the 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...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.46 |
| _version_ | 1811244053386231808 |
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| author | Martin Vrbický Karel Macek Jaroslav Pochobradský Jan Svoboda Miloš Sedlák Pavel Drabina |
| author_facet | Martin Vrbický Karel Macek Jaroslav Pochobradský Jan Svoboda Miloš Sedlák Pavel Drabina |
| author_sort | Martin Vrbický |
| collection | DOAJ |
| description | The human drugs – the 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 of these drugs was studied in detail. Highly enantioselective catalysts were tested in the key step of the synthetic procedure, i.e., the asymmetric Henry reaction, under different reaction conditions, using several starting aldehydes. The corresponding nitroaldols as chiral intermediates in the syntheses of these drugs were obtained in high yields and enantiomeric excesses of up to 91% ee. |
| first_indexed | 2024-04-12T14:19:16Z |
| format | Article |
| id | doaj.art-eb7b560020e747b7bdf27cc618575c9e |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-12T14:19:16Z |
| publishDate | 2022-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-eb7b560020e747b7bdf27cc618575c9e2022-12-22T03:29:39ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-04-0118143844510.3762/bjoc.18.461860-5397-18-46The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxabanMartin Vrbický0Karel Macek1Jaroslav Pochobradský2Jan Svoboda3Miloš Sedlák4Pavel Drabina5Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech RepublicThe human drugs – the 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 of these drugs was studied in detail. Highly enantioselective catalysts were tested in the key step of the synthetic procedure, i.e., the asymmetric Henry reaction, under different reaction conditions, using several starting aldehydes. The corresponding nitroaldols as chiral intermediates in the syntheses of these drugs were obtained in high yields and enantiomeric excesses of up to 91% ee.https://doi.org/10.3762/bjoc.18.46asymmetric henry reactionenantioselective catalysislinezolidoxazolidine-2-one derivativesrivaroxaban |
| spellingShingle | Martin Vrbický Karel Macek Jaroslav Pochobradský Jan Svoboda Miloš Sedlák Pavel Drabina The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban Beilstein Journal of Organic Chemistry asymmetric henry reaction enantioselective catalysis linezolid oxazolidine-2-one derivatives rivaroxaban |
| title | The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| title_full | The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| title_fullStr | The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| title_full_unstemmed | The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| title_short | The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| title_sort | asymmetric henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban |
| topic | asymmetric henry reaction enantioselective catalysis linezolid oxazolidine-2-one derivatives rivaroxaban |
| url | https://doi.org/10.3762/bjoc.18.46 |
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