Autor según el artículo: Cataffo, A; Pena-Lopez, M; Pedrazzani, R; Echavarren, AM
Departamento: Química Analítica i Química Orgànica
Autor/es de la URV: Cataffo, Andrea / ECHAVARREN PABLOS, ANTONIO
Palabras clave: 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
Resumen: 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.
Áreas temáticas: 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
Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
Direcció de correo del autor: antoniomaria.echavarren@urv.cat andrea.cataffo@estudiants.urv.cat
Identificador del autor: 0000-0002-6418-7930
Fecha de alta del registro: 2024-01-13
Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
Enlace a la fuente original: https://onlinelibrary.wiley.com/doi/10.1002/anie.202312874
URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/
Referencia al articulo segun fuente origial: Angewandte Chemie (International Ed. Print). 62 (49): e202312874-
Referencia 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 del artículo: 10.1002/anie.202312874
Entidad: Universitat Rovira i Virgili
Año de publicación de la revista: 2023
Tipo de publicación: Journal Publications
Repositori URV