Author, as appears in the article.: Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L.; Fernandez, Elena;

Department: Química Física i Inorgànica

URV's Author/s: Fernández Gutiérrez, Maria Elena

Keywords: Transannular borylation Stereogenic alkyl boronate Ring closing Esters Electrophilic intramolecular trapping Cyclization Copper(i)-catalyzed reaction Copper catalysts stereogenic alkyl boronate ring closing electrophilic intramolecular trapping copper catalysts

Abstract: Medium-sized carbocycles containing an alpha,beta-unsaturated ketone moiety as Michael acceptor site and a ketone moiety as internal electrophilic site are ideal substrates to conduct Cu(I)-catalyzed conjugated borylation followed by electrophilic intramolecular trapping that results into a pioneer transannular borylative ring closing reaction. The relative configuration of three adjacent stereocenters is controlled, giving access to a single diastereoisomer for a wide range of substrates tested. Moreover, when a chiral ligand is incorporated, the reaction provides enantioenriched polycyclic products with up to 99 % ee.

Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 14337851

Author's mail: mariaelena.fernandez@urv.cat

Author identifier: 0000-0001-9025-1791

Record's date: 2023-02-18

Papper version: info:eu-repo/semantics/acceptedVersion

Link to the original source: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201913438

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

Papper original source: Angewandte Chemie (International Ed. Print). 59 (5): 2100-2104

APA: Sendra, Jana; Manzano, Ruben; Reyes, Efraim; Vicario, Jose L.; Fernandez, Elena; (2020). Catalytic Stereoselective Borylative Transannular Reactions. Angewandte Chemie (International Ed. Print), 59(5), 2100-2104. DOI: 10.1002/anie.201913438

Article's DOI: 10.1002/anie.201913438

Entity: Universitat Rovira i Virgili

Journal publication year: 2020

Publication Type: Journal Publications