Author, as appears in the article.: Martin-Torres, Inmaculada; Ogalla, Gala; Yang, Jin-Ming; Rinaldi, Antonia; Echavarren, Antonio M.;
Department: Química Analítica i Química Orgànica
URV's Author/s: ECHAVARREN PABLOS, ANTONIO / Martín Torres, Inmaculada / Ogalla Estévez, Gala
Keywords: Total synthesis Theoretical study Synthesis (chemical) Natural product synthesis Gold(i) cavitands Gold compounds Gold complexes Enantioselectivity Enantioselective Cycloisomerizations Cyclization Cavity effect Asymmetric synthesis Alkoxycyclization 1 ,6-enynes
Abstract: Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.
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 inmaculada.martin@estudiants.urv.cat gala.ogalla@estudiants.urv.cat
Author identifier: 0000-0002-6418-7930
Record's date: 2024-07-27
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202017035
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Angewandte Chemie (International Ed. Print). 60 (17): 9339-9344
APA: Martin-Torres, Inmaculada; Ogalla, Gala; Yang, Jin-Ming; Rinaldi, Antonia; Echavarren, Antonio M.; (2021). Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C. Angewandte Chemie (International Ed. Print), 60(17), 9339-9344. DOI: 10.1002/anie.202017035
Article's DOI: 10.1002/anie.202017035
Entity: Universitat Rovira i Virgili
Journal publication year: 2021
Publication Type: Journal Publications
Repositori URV