Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone
The asymmetric formal [3 + 3] annulation process of (<i>E</i>)-2-(3-phenylacryloyl)pyridine <i>N</i>-oxide with benzyl methyl ketone was investigated. The possibility of a stereoselective outcome was checked using salts of natural amino acids, as well as chiral bifunctional d...
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MDPI AG
2024-01-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/16/1/104 |
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| author | Zuzanna Wrzeszcz Jakub A. Warachim Renata Siedlecka |
| author_facet | Zuzanna Wrzeszcz Jakub A. Warachim Renata Siedlecka |
| author_sort | Zuzanna Wrzeszcz |
| collection | DOAJ |
| description | The asymmetric formal [3 + 3] annulation process of (<i>E</i>)-2-(3-phenylacryloyl)pyridine <i>N</i>-oxide with benzyl methyl ketone was investigated. The possibility of a stereoselective outcome was checked using salts of natural amino acids, as well as chiral bifunctional derivatives containing amino groups and thiourea or squaramide fragments as organocatalysts. Different types of organocatalysts applied led to opposite enantiomers of 2-(3-oxo-4,5-diphenyl-cyclohex-1-en-yl)pyridine 1-oxide (up to 60% ee). Spectroscopic analysis of the isolated product and analysis of the reaction course was carried out, taking into account the obtained regio- and stereoselectivity. In order to verify the postulated results, calculations of the energy of the intermediate reaction products and the final product using the Kohn–Sham Density Functional Theory (KS-DFT) were made. |
| first_indexed | 2024-03-08T10:34:13Z |
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| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-08T10:34:13Z |
| publishDate | 2024-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-3b5ca41601b54646bacb565b634175082024-01-26T18:38:55ZengMDPI AGSymmetry2073-89942024-01-0116110410.3390/sym16010104Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl KetoneZuzanna Wrzeszcz0Jakub A. Warachim1Renata Siedlecka2Department of Organic and Medicinal Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw, PolandInstitute of Advanced Materials, Faculty of Chemistry, Wroclaw University of Science and Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw, PolandDepartment of Organic and Medicinal Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw, PolandThe asymmetric formal [3 + 3] annulation process of (<i>E</i>)-2-(3-phenylacryloyl)pyridine <i>N</i>-oxide with benzyl methyl ketone was investigated. The possibility of a stereoselective outcome was checked using salts of natural amino acids, as well as chiral bifunctional derivatives containing amino groups and thiourea or squaramide fragments as organocatalysts. Different types of organocatalysts applied led to opposite enantiomers of 2-(3-oxo-4,5-diphenyl-cyclohex-1-en-yl)pyridine 1-oxide (up to 60% ee). Spectroscopic analysis of the isolated product and analysis of the reaction course was carried out, taking into account the obtained regio- and stereoselectivity. In order to verify the postulated results, calculations of the energy of the intermediate reaction products and the final product using the Kohn–Sham Density Functional Theory (KS-DFT) were made.https://www.mdpi.com/2073-8994/16/1/104azaaromatic <i>N</i>-oxidesorganocatalysisannulation reactionstereoselectivity |
| spellingShingle | Zuzanna Wrzeszcz Jakub A. Warachim Renata Siedlecka Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone Symmetry azaaromatic <i>N</i>-oxides organocatalysis annulation reaction stereoselectivity |
| title | Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone |
| title_full | Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone |
| title_fullStr | Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone |
| title_full_unstemmed | Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone |
| title_short | Selectivity in Catalytic Asymmetric Formal [3 + 3] Annulation of 2-Enoyl-pyridine <i>N</i>-Oxide with Benzyl Methyl Ketone |
| title_sort | selectivity in catalytic asymmetric formal 3 3 annulation of 2 enoyl pyridine i n i oxide with benzyl methyl ketone |
| topic | azaaromatic <i>N</i>-oxides organocatalysis annulation reaction stereoselectivity |
| url | https://www.mdpi.com/2073-8994/16/1/104 |
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