Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data
The direct oxidation reaction of isoxazolidines plays an important role in organic chemistry, leading to the synthesis of biologically active compounds. In this paper, we report a computational mechanistic study of RuO<sub>4</sub>-catalyzed oxidation of differently <i>N</i>-s...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5390 |
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| author | Laura Legnani Salvatore V. Giofré Daniela Iannazzo Consuelo Celesti Lucia Veltri Maria Assunta Chiacchio |
| author_facet | Laura Legnani Salvatore V. Giofré Daniela Iannazzo Consuelo Celesti Lucia Veltri Maria Assunta Chiacchio |
| author_sort | Laura Legnani |
| collection | DOAJ |
| description | The direct oxidation reaction of isoxazolidines plays an important role in organic chemistry, leading to the synthesis of biologically active compounds. In this paper, we report a computational mechanistic study of RuO<sub>4</sub>-catalyzed oxidation of differently <i>N</i>-substituted isoxazolidines <b>1a</b>–<b>c</b>. Attention was focused on the endo/exo oxidation selectivity. For all the investigated compounds, the exo attack is preferred to the endo one, showing exo percentages growing in parallel with the stability order of transient carbocations found along the reaction pathway. The study has been supported by experimental data that nicely confirm the modeling results. |
| first_indexed | 2024-03-10T01:32:04Z |
| format | Article |
| id | doaj.art-e07a83ed0463470f915bc3509c487c4e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:32:04Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e07a83ed0463470f915bc3509c487c4e2023-11-23T13:41:11ZengMDPI AGMolecules1420-30492022-08-012717539010.3390/molecules27175390Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental DataLaura Legnani0Salvatore V. Giofré1Daniela Iannazzo2Consuelo Celesti3Lucia Veltri4Maria Assunta Chiacchio5Dipartimento di Biotecnologie e Bioscienze, Università di Milano-Bicocca, Piazza della Scienza 2, 20126 Milano, ItalyDipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università di Messina, Viale F. Stagno D’Alcontres, 98166 Messina, ItalyDipartimento di Ingegneria, Università di Messina, Contrada di Dio, 98166 Messina, ItalyDipartimento di Ingegneria, Università di Messina, Contrada di Dio, 98166 Messina, ItalyDipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via Pietro Bucci 12/C, 87036 Aracavacata di Rende, ItalyDipartimento di Scienze del Farmaco e della Salute, Università di Catania, Viale A. Doria 6, 95125 Catania, ItalyThe direct oxidation reaction of isoxazolidines plays an important role in organic chemistry, leading to the synthesis of biologically active compounds. In this paper, we report a computational mechanistic study of RuO<sub>4</sub>-catalyzed oxidation of differently <i>N</i>-substituted isoxazolidines <b>1a</b>–<b>c</b>. Attention was focused on the endo/exo oxidation selectivity. For all the investigated compounds, the exo attack is preferred to the endo one, showing exo percentages growing in parallel with the stability order of transient carbocations found along the reaction pathway. The study has been supported by experimental data that nicely confirm the modeling results.https://www.mdpi.com/1420-3049/27/17/5390ruthenium tetroxideoxidationDFT calculations3-isoxazolidinonechemoselectivity |
| spellingShingle | Laura Legnani Salvatore V. Giofré Daniela Iannazzo Consuelo Celesti Lucia Veltri Maria Assunta Chiacchio Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data Molecules ruthenium tetroxide oxidation DFT calculations 3-isoxazolidinone chemoselectivity |
| title | Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data |
| title_full | Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data |
| title_fullStr | Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data |
| title_full_unstemmed | Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data |
| title_short | Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data |
| title_sort | chemoselective oxidation of isoxazolidines with ruthenium tetroxide a successful intertwining of combined theoretical and experimental data |
| topic | ruthenium tetroxide oxidation DFT calculations 3-isoxazolidinone chemoselectivity |
| url | https://www.mdpi.com/1420-3049/27/17/5390 |
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