Author, as appears in the article.: Borràs C; Elías-Rodríguez P; Carmona A; Robina I; Pàmies O; Diéguez M
Department: Química Física i Inorgànica
URV's Author/s: BORRÀS NOGUERA, CARLOTA / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
Keywords: Clean water and sanitation
Abstract: © 2018 American Chemical Society. The construction of a novel class of amino-phosphite/phosphinite/phosphine ligands containing a protected pyrrolidine-3,4-diol moiety is presented. These ligands are obtained from readily available sugars. They thus contain the advantages of carbohydrates in terms of selection of the stereogenic carbons, polyfunctional groups able to modulate the electronic and steric properties, and the general good stability of carbohydrate derivatives. They constitute a novel class of P,N-ligands that have been used in the enantioselective allylic substitutions of acyclic and cyclic substrates with varied electronic and steric requirements, using different C- and N-nucleophiles, with high enantioselectivities. Among the three groups of P,N-ligands (amino-P; P = phosphite, phosphinite, and phosphine groups) the new amino-phosphite ligands give the widest substrate and nucleophile scope, including the more challenging hindered linear and cyclic substrates. In particular, for carbohydrate-derived amino-phosphite ligands and linear substrates, high enantioselectivity in the reactions requires an R configuration of the binaphthyl moiety. However, for cyclic substrates both product enantiomers can be reached by setting out the chirality of the binaphthyl phosphite moiety. A detailed investigation of the appropriate Pd intermediates is also presented.
Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Materiais Inorganic chemistry Engenharias ii Ciências biológicas ii Ciências agrárias i Chemistry, organic Chemistry, inorganic & nuclear Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 0276-7333
Author's mail: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
Author identifier: 0000-0002-2352-8508 0000-0002-8450-0656
Last page: 1694
Record's date: 2024-11-16
Journal volume: 37
Papper version: info:eu-repo/semantics/submittedVersion
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00140
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Organometallics. 37 (11): 1682-1694
APA: Borràs C; Elías-Rodríguez P; Carmona A; Robina I; Pàmies O; Diéguez M (2018). Amino-P Ligands from Iminosugars: New Readily Available and Modular Ligands for Enantioselective Pd-Catalyzed Allylic Substitutions. Organometallics, 37(11), 1682-1694. DOI: 10.1021/acs.organomet.8b00140
Article's DOI: 10.1021/acs.organomet.8b00140
Entity: Universitat Rovira i Virgili
Journal publication year: 2018
First page: 1682
Publication Type: Journal Publications