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

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

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

Article's DOI: 10.1021/acs.orglett.9b03672

Entity: Universitat Rovira i Virgili

Journal publication year: 2019

First page: 9247

Publication Type: Journal Publications