Author, as appears in the article.: Salvado, Oriol; Dominguez-Molano, Paula; Fernandez, Elena;
Department: Química Física i Inorgànica
URV's Author/s: Domínguez Molano, Paula / Fernández Gutiérrez, Maria Elena / Salvadó Ruiz, Oriol
Keywords: Reagents Hydroboration Esters Carbenoids Asymmetric cyclopropanation Access
Abstract: Palladium catalyzes the cydclopropanation of 2-substituted 1,1-diborylalkenes with (trimethylsilyl)diazomethane. The relative stereoselectivity is controlled via a carbene insertion sequence generating an exclusive anti conformation between the R and SiMe3 substituents. Mixed 1,1-diborylalkenes also contributed to the formation of stereoselective B, B, Si-cyclopropanes. Orthogonal activation with (NaOBu)-Bu-t gives protodeborylation preferentially on the boron moiety syn to the aryl group. Further oxidation gives access to polyfunctional cycloopropyl alcohols with controlled enantioselectivity when chiral boryl motifs are involved.
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/
Author's mail: oriol.salvado@urv.cat paula.dominguez@urv.cat mariaelena.fernandez@urv.cat oriol.salvado@urv.cat paula.dominguez@urv.cat
Author identifier: 0000-0001-9025-1791
Record's date: 2024-01-13
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.2c01885
Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Organic Letters. 24 (27): 4949-4953
APA: Salvado, Oriol; Dominguez-Molano, Paula; Fernandez, Elena; (2022). Stereoselective Cyclopropanation of 1,1-Diborylalkenes via Palladium-Catalyzed (Trimethylsilyl)diazomethane Insertion. Organic Letters, 24(27), 4949-4953. DOI: 10.1021/acs.orglett.2c01885
Article's DOI: 10.1021/acs.orglett.2c01885
Entity: Universitat Rovira i Virgili
Journal publication year: 2022
Publication Type: Journal Publications
Repositori URV