Author, as appears in the article.: Pamies, Oscar; Margalef, Jessica; Canellas, Santiago; James, Jinju; Judge, Eric; Guiry, Patrick J; Moberg, Christina; Backvall, Jan-E; Pfaltz, Andreas; Pericas, Miquel A; Dieguez, Montserrat
Department: Química Física i Inorgànica
URV's Author/s: Diéguez Fernández, Montserrat / MARGALEF LLEBARIA, JOAQUIM / Pamies Ollé, Oscar / Pericàs Brondo, Miquel Àngel
Keywords: Transition-metal Phosphite-oxazoline ligands Linked bis(oxazoline) ligands Kinetic resolution Force-field parameters Chiral diaminophosphine oxide Carbon quaternary stereocenters C-h oxidation Asymmetric 3+2 cycloaddition Alkylation total-synthesis
Abstract: This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.
Thematic Areas: Química Materiais General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas ii Ciências biológicas i Ciência de alimentos Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Biotecnología
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: miquelangel.pericas@urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
Record's date: 2024-11-09
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.chemrev.0c00736
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Chemical Reviews. 121 (8): 4373-4505
APA: Pamies, Oscar; Margalef, Jessica; Canellas, Santiago; James, Jinju; Judge, Eric; Guiry, Patrick J; Moberg, Christina; Backvall, Jan-E; Pfaltz, Andreas (2021). Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications. Chemical Reviews, 121(8), 4373-4505. DOI: 10.1021/acs.chemrev.0c00736
Article's DOI: 10.1021/acs.chemrev.0c00736
Entity: Universitat Rovira i Virgili
Journal publication year: 2021
Publication Type: Journal Publications