Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions
A series of new bidentate <i>N,S</i>-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition...
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| Language: | English |
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MDPI AG
2021-03-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/13/3/502 |
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| author | Agata J. Pacuła-Miszewska Anna Laskowska Anna Kmieciak Mariola Zielińska-Błajet Marek P. Krzemiński Jacek Ścianowski |
| author_facet | Agata J. Pacuła-Miszewska Anna Laskowska Anna Kmieciak Mariola Zielińska-Błajet Marek P. Krzemiński Jacek Ścianowski |
| author_sort | Agata J. Pacuła-Miszewska |
| collection | DOAJ |
| description | A series of new bidentate <i>N,S</i>-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions. |
| first_indexed | 2024-03-10T13:05:58Z |
| format | Article |
| id | doaj.art-91a7502053a44d098e54b092c18ec477 |
| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-10T13:05:58Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-91a7502053a44d098e54b092c18ec4772023-11-21T11:07:47ZengMDPI AGSymmetry2073-89942021-03-0113350210.3390/sym13030502Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric ReactionsAgata J. Pacuła-Miszewska0Anna Laskowska1Anna Kmieciak2Mariola Zielińska-Błajet3Marek P. Krzemiński4Jacek Ścianowski5Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, PolandDepartment of Organic and Medicinal Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego Street, 50-370 Wrocław, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, PolandA series of new bidentate <i>N,S</i>-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.https://www.mdpi.com/2073-8994/13/3/502aziridine<i>N,S</i>-ligandsasymmetric synthesisdiethylzinc additionphenylethynylzinc additionTsuji–Trost reaction |
| spellingShingle | Agata J. Pacuła-Miszewska Anna Laskowska Anna Kmieciak Mariola Zielińska-Błajet Marek P. Krzemiński Jacek Ścianowski Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions Symmetry aziridine <i>N,S</i>-ligands asymmetric synthesis diethylzinc addition phenylethynylzinc addition Tsuji–Trost reaction |
| title | Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions |
| title_full | Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions |
| title_fullStr | Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions |
| title_full_unstemmed | Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions |
| title_short | Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions |
| title_sort | chiral aziridine sulfide i n sp3 s i ligands for metal catalyzed asymmetric reactions |
| topic | aziridine <i>N,S</i>-ligands asymmetric synthesis diethylzinc addition phenylethynylzinc addition Tsuji–Trost reaction |
| url | https://www.mdpi.com/2073-8994/13/3/502 |
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