Recent advances in organocatalytic atroposelective reactions
Axial chirality is present in a variety of naturally occurring compounds, and is becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of...
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Beilstein-Institut
2025-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.6 |
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| author | Henrich Szabados Radovan Šebesta |
| author_facet | Henrich Szabados Radovan Šebesta |
| author_sort | Henrich Szabados |
| collection | DOAJ |
| description | Axial chirality is present in a variety of naturally occurring compounds, and is becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of axially chiral compounds via asymmetric organocatalysis. Atroposelective organocatalytic reactions are discussed according to the dominant catalyst activation mode. For covalent organocatalysis, the typical enamine and iminium modes are presented, followed by N-heterocyclic carbene-catalyzed reactions. The bulk of the review is devoted to non-covalent activation, where chiral Brønsted acids feature as the most prolific catalytic structure. The last part of the article discusses hydrogen-bond-donating catalysts and other catalyst motifs such as phase-transfer catalysts. |
| format | Article |
| id | doaj-art-a92e55eb0e7a482190992d362a898316 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-a92e55eb0e7a482190992d362a8983162025-02-03T09:10:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-01-012115512110.3762/bjoc.21.61860-5397-21-6Recent advances in organocatalytic atroposelective reactionsHenrich Szabados0Radovan Šebesta1Department of Organic Chemistry, Faculty of Natural Science, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Department of Organic Chemistry, Faculty of Natural Science, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia Axial chirality is present in a variety of naturally occurring compounds, and is becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of axially chiral compounds via asymmetric organocatalysis. Atroposelective organocatalytic reactions are discussed according to the dominant catalyst activation mode. For covalent organocatalysis, the typical enamine and iminium modes are presented, followed by N-heterocyclic carbene-catalyzed reactions. The bulk of the review is devoted to non-covalent activation, where chiral Brønsted acids feature as the most prolific catalytic structure. The last part of the article discusses hydrogen-bond-donating catalysts and other catalyst motifs such as phase-transfer catalysts.https://doi.org/10.3762/bjoc.21.6asymmetric organocatalysisatropoisomersatroposelective synthesisaxial chiralitystereogenic axis |
| spellingShingle | Henrich Szabados Radovan Šebesta Recent advances in organocatalytic atroposelective reactions Beilstein Journal of Organic Chemistry asymmetric organocatalysis atropoisomers atroposelective synthesis axial chirality stereogenic axis |
| title | Recent advances in organocatalytic atroposelective reactions |
| title_full | Recent advances in organocatalytic atroposelective reactions |
| title_fullStr | Recent advances in organocatalytic atroposelective reactions |
| title_full_unstemmed | Recent advances in organocatalytic atroposelective reactions |
| title_short | Recent advances in organocatalytic atroposelective reactions |
| title_sort | recent advances in organocatalytic atroposelective reactions |
| topic | asymmetric organocatalysis atropoisomers atroposelective synthesis axial chirality stereogenic axis |
| url | https://doi.org/10.3762/bjoc.21.6 |
| work_keys_str_mv | AT henrichszabados recentadvancesinorganocatalyticatroposelectivereactions AT radovansebesta recentadvancesinorganocatalyticatroposelectivereactions |