Author, as appears in the article.: Gava, Riccardo; Fernandez, Elena
Department: Química Física i Inorgànica
URV's Author/s: Fernández Gutiérrez, Maria Elena
Keywords: S(n)2 mechanism S 2 mechanism n Lithium salts Ketones Insertion Homoallylboronates Geminal diborylalkanes Gem-silylborylation Esters Diborylalkanes Diboronates Deprotonation Carbanions Alkyl-halides Aldehydes Access sn2 mechanism homoallylboronates geminal diborylalkanes diboronates
Abstract: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Vinyl epoxides and styrene oxide can react with diborylmethide lithium salts through an exclusive SN2 borylmethylation/ring opening in a regio- and diastereoselective way, depending on the nature of the substrate. The ring-opening protocol provides homoallylboronates that can be transformed into challenging diastereomeric bishomoallylic alicyclic 1,3-diols. Unprecedented 3-borylated 1,2-oxaborolan-2-ol products were prepared by borylmethylation/ring opening of 2-methyl-2-vinyloxirane followed by intramolecular cyclization.
Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 15213765
Author's mail: mariaelena.fernandez@urv.cat
Author identifier: 0000-0001-9025-1791
Record's date: 2023-07-31
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201901406
Papper original source: Chemistry-A European Journal. 25 (34): 8013-8017
APA: Gava, Riccardo; Fernandez, Elena (2019). Selective C-C coupling of vinyl epoxides with diborylmethide lithium salts. Chemistry-A European Journal, 25(34), 8013-8017. DOI: 10.1002/chem.201901406
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Article's DOI: 10.1002/chem.201901406
Entity: Universitat Rovira i Virgili
Journal publication year: 2019
Publication Type: Journal Publications
Repositori URV