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: @infoAeu @residentesaeu @uroweb Etiqueta «#» Hashtag

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: montserrat.dieguez@urv.cat oscar.pamies@urv.cat

Author identifier: 0000-0002-8450-0656 0000-0002-2352-8508

Last page: 1694

Record's date: 2023-02-18

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: http://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