Autor segons l'article: Cataffo, A; Pena-Lopez, M; Pedrazzani, R; Echavarren, AM
Departament: Química Analítica i Química Orgànica
Autor/s de la URV: Cataffo, Andrea / ECHAVARREN PABLOS, ANTONIO
Paraules clau: Spirocyclic ketones Intermolecular 2+2 cycloaddition Gold catalysis Enynes Chiral auxiliaries Alkoxycyclization unique spirocyclic ketones rearrangement gold catalysis enynes enantioselective construction cycloisomerizations chiral auxiliaries catalyzed reaction c-n alkynes alkenes
Resum: Two different classes of stereoselective cyclizations have been developed using a chiral auxiliary approach with commercially available [JohnPhosAu(MeCN)SbF6] as catalyst. First, a stereoselective cascade cyclization of 1,5-enynes was achieved using the Oppolzer camphorsultam as chiral auxiliary. In this case, a one-pot cyclization-hydrolysis sequence was developed to directly afford enantioenriched spirocyclic ketones. Then, the stereoselective alkoxycyclization of 1,6-enynes was mediated by an Evans-type oxazolidinone. A reduction-hydrolysis sequence was selected to remove the auxiliary to give enantioenriched β-tetralones. DFT studies confirmed that the steric clash between the chiral auxiliary and alkene accounts for the experimentally observed diastereoselective cyclization through the Si face.
Àrees temàtiques: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat andrea.cataffo@estudiants.urv.cat
Identificador de l'autor: 0000-0002-6418-7930
Data d'alta del registre: 2024-08-03
Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
Enllaç font original: https://onlinelibrary.wiley.com/doi/10.1002/anie.202312874
URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
Referència a l'article segons font original: Angewandte Chemie (International Ed. Print). 62 (49): e202312874-
Referència de l'ítem segons les normes APA: Cataffo, A; Pena-Lopez, M; Pedrazzani, R; Echavarren, AM (2023). Chiral Auxiliary Approach for Gold(I)-Catalyzed Cyclizations. Angewandte Chemie (International Ed. Print), 62(49), e202312874-. DOI: 10.1002/anie.202312874
DOI de l'article: 10.1002/anie.202312874
Entitat: Universitat Rovira i Virgili
Any de publicació de la revista: 2023
Tipus de publicació: Journal Publications
Repositori URV