Author, as appears in the article.: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M
Department: Química Física i Inorgànica
URV's Author/s: Besora Bonet, Maria / Biosca Brull, Maria / Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar / Saltó De La Torre, Joan
Keywords: Hashtag Etiqueta «#» @uroweb @residentesaeu @infoAeu
Abstract: © 2018 American Chemical Society. A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.
Thematic Areas: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 21555435
Author's mail: maria.biosca@urv.cat maria.besora@urv.cat joan.salto@estudiants.urv.cat joan.salto@estudiants.urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
Author identifier: 0000-0002-9116-6318 0000-0002-6656-5827 0000-0003-4846-8473 0000-0003-4846-8473 0000-0002-2352-8508 0000-0002-8450-0656
Last page: 3601
Record's date: 2024-09-07
Journal volume: 8
Papper version: info:eu-repo/semantics/submittedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acscatal.7b04192
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Acs Catalysis. 8 (4): 3587-3601
APA: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M (2018). Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions. Acs Catalysis, 8(4), 3587-3601. DOI: 10.1021/acscatal.7b04192
Article's DOI: 10.1021/acscatal.7b04192
Entity: Universitat Rovira i Virgili
Journal publication year: 2018
First page: 3587
Publication Type: Journal Publications