Repositori institucional URV
| URV's Author/s: | Fernández Gutiérrez, Maria Elena |
| Author, as appears in the article.: | Salvado, Oriol; Gava, Riccardo; Fernandez, Elena |
| Author's mail: | mariaelena.fernandez@urv.cat |
| Author identifier: | 0000-0001-9025-1791 |
| Journal publication year: | 2019 |
| Publication Type: | Journal Publications |
| ISSN: | 1523-7060 |
| APA: | Salvado, Oriol; Gava, Riccardo; Fernandez, Elena (2019). Diborylalkyllithium Salts Trigger Regioselective Ring Opening of Vinyl Aziridines. Organic Letters, 21(22), 9247-9250. DOI: 10.1021/acs.orglett.9b03672 |
| Paper original source: | Organic Letters. 21 (22): 9247-9250 |
| Abstract: | gem-Diborylalkanes treated with LiTMP produce alpha-diborylalkane lithium bases that perform nucleophilic attack on vinyl aziridines with controlled regioselectivity. Preferred S(N)2 diborylalkylation ring opening reaction on the less sterically hindered position is observed with 1-tosyl-2-vinylaziridine, whereas exclusive S(N)2' nucleophilic attack occurs on 2-methyl-1-tosyl-2-vinylaziridine. Cyclic vinyl aziridines interact through a third venue, via S(N)2 diborylalkylation ring opening reaction on the allylic position. Homoallylic diboronates are formed with complete stereochemical control. |
| Article's DOI: | 10.1021/acs.orglett.9b03672 |
| Link to the original source: | https://pubs.acs.org/doi/10.1021/acs.orglett.9b03672 |
| Paper version: | info:eu-repo/semantics/acceptedVersion |
| licence for use: | https://creativecommons.org/licenses/by/3.0/es/ |
| Department: | Química Física i Inorgànica |
| Licence document URL: | https://repositori.urv.cat/ca/proteccio-de-dades/ |
| Thematic Areas: | Química Physical and theoretical chemistry Organic chemistry Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry |
| Keywords: | Substitution Protodeboronation Epoxides Borylation Acids |
| Entity: | Universitat Rovira i Virgili |
| Record's date: | 2025-02-18 |
| First page: | 9247 |
| Last page: | 9250 |
| Journal volume: | 21 |
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