Autor segons l'article: Echavarren, A.M.; Herlé, B.; Holstein, P.M.
Departament: Química Analítica i Química Orgànica
Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO MARIA; Herlé, B.; Holstein, P.M.
Paraules clau: cycloheptatrienes cyclopropanation Gold catalysis
Resum: A highly stereoselective gold(I)-catalyzed cis-vinylcyclopropanation of alkenes has been developed. Allylic gold carbenes, generated via a retro-Buchner reaction of 7-alkenyl-1,3,5-cycloheptatrienes, react with alkenes to form vinylcyclopropanes. The gold(I)-catalyzed retro-Buchner reaction of these substrates proceeds by simple heating at a temperature much lower than that required for the reaction of 7-aryl-1,3,5-cycloheptatrienes (75 °C vs 120 °C). A newly developed Julia-Kocienski reagent enables the synthesis of the required cycloheptatriene derivatives in one step from readily available aldehydes or ketones. On the basis of mechanistic investigations, a stereochemical model for the cis selectivity was proposed. An unprecedented gold-catalyzed isomerization of cis- to trans-cyclopropanes has also been discovered and studied by DFT calculations.
Àrees temàtiques: Química Química Chemistry
Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 2155-5435
Identificador de l'autor: 0000-0001-6808-3007; ;
Data d'alta del registre: 2017-10-19
Pàgina final: 3675
Volum de revista: 7
Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
Enllaç font original: http://pubs.acs.org/doi/abs/10.1021/acscatal.7b00737
Programa de finançament: euratom; European Research Council; ERC; 321066 european; MINECO/FEDER, UE; CTQ2016-75960-P MINECO-Severo Ochoa Excellence Acreditation 2014-2018; SEV; SEV-2013-0319 altres; Grups consolidats Generalitat de Catalunya; SGR; 2014 SGR 818
URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
DOI de l'article: 10.1021/acscatal.7b00737
Entitat: Universitat Rovira i Virgili
Any de publicació de la revista: 2017
Pàgina inicial: 3668
Tipus de publicació: Article Artículo Article
Repositori URV