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

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

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

Article's DOI: 10.1002/chem.201901406

Entity: Universitat Rovira i Virgili

Journal publication year: 2019

Publication Type: Journal Publications