Author, as appears in the article.: Salvado, Oriol; Gava, Riccardo; Fernandez, Elena;
Department: Química Física i Inorgànica
URV's Author/s: Fernández Gutiérrez, Maria Elena
Keywords: Substitution Protodeboronation Epoxides Borylation Acids
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.
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
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 1523-7060
Author's mail: mariaelena.fernandez@urv.cat
Author identifier: 0000-0001-9025-1791
Last page: 9250
Record's date: 2023-02-18
Journal volume: 21
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.9b03672
Papper original source: Organic Letters. 21 (22): 9247-9250
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
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Article's DOI: 10.1021/acs.orglett.9b03672
Entity: Universitat Rovira i Virgili
Journal publication year: 2019
First page: 9247
Publication Type: Journal Publications
Repositori URV