Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies
The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report e...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/23/7399 |
| _version_ | 1827674720771768320 |
|---|---|
| author | Lucilla Favero Andrea Menichetti Cosimo Boldrini Lucrezia Margherita Comparini Valeria Di Bussolo Sebastiano Di Pietro Mauro Pineschi |
| author_facet | Lucilla Favero Andrea Menichetti Cosimo Boldrini Lucrezia Margherita Comparini Valeria Di Bussolo Sebastiano Di Pietro Mauro Pineschi |
| author_sort | Lucilla Favero |
| collection | DOAJ |
| description | The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B<sub>2</sub>pin<sub>2</sub>) in a regioselective nucleophilic addition reaction under copper catalysis. |
| first_indexed | 2024-03-10T04:47:11Z |
| format | Article |
| id | doaj.art-40f7f75adbd0457eaee6b5496f3ba918 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T04:47:11Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-40f7f75adbd0457eaee6b5496f3ba9182023-11-23T02:51:59ZengMDPI AGMolecules1420-30492021-12-012623739910.3390/molecules26237399Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational StudiesLucilla Favero0Andrea Menichetti1Cosimo Boldrini2Lucrezia Margherita Comparini3Valeria Di Bussolo4Sebastiano Di Pietro5Mauro Pineschi6Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyThe possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B<sub>2</sub>pin<sub>2</sub>) in a regioselective nucleophilic addition reaction under copper catalysis.https://www.mdpi.com/1420-3049/26/23/7399copper catalysisdiboron reagentsaziridinesaminoboronatesDFT study |
| spellingShingle | Lucilla Favero Andrea Menichetti Cosimo Boldrini Lucrezia Margherita Comparini Valeria Di Bussolo Sebastiano Di Pietro Mauro Pineschi Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies Molecules copper catalysis diboron reagents aziridines aminoboronates DFT study |
| title | Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies |
| title_full | Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies |
| title_fullStr | Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies |
| title_full_unstemmed | Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies |
| title_short | Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B<sub>2</sub>pin<sub>2</sub>: Experimental and Computational Studies |
| title_sort | copper catalyzed ring opening reactions of alkyl aziridines with b sub 2 sub pin sub 2 sub experimental and computational studies |
| topic | copper catalysis diboron reagents aziridines aminoboronates DFT study |
| url | https://www.mdpi.com/1420-3049/26/23/7399 |
| work_keys_str_mv | AT lucillafavero coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT andreamenichetti coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT cosimoboldrini coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT lucreziamargheritacomparini coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT valeriadibussolo coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT sebastianodipietro coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies AT mauropineschi coppercatalyzedringopeningreactionsofalkylaziridineswithbsub2subpinsub2subexperimentalandcomputationalstudies |