Author, as appears in the article.: Cataffo, A; Pena-Lopez, M; Pedrazzani, R; Echavarren, AM
Department: Química Analítica i Química Orgànica
URV's Author/s: Cataffo, Andrea / ECHAVARREN PABLOS, ANTONIO
Keywords: 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
Abstract: 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.
Thematic Areas: 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
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: antoniomaria.echavarren@urv.cat andrea.cataffo@estudiants.urv.cat
Author identifier: 0000-0002-6418-7930
Record's date: 2024-08-03
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202312874
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Angewandte Chemie (International Ed. Print). 62 (49): e202312874-
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
Article's DOI: 10.1002/anie.202312874
Entity: Universitat Rovira i Virgili
Journal publication year: 2023
Publication Type: Journal Publications
Repositori URV