dc.contributor.author | Riaño Castela, Iker | |
dc.contributor.author | Uria Pujana, Uxue | |
dc.contributor.author | Reyes Martín, Efraim | |
dc.contributor.author | Carrillo Fernández, María Luisa | |
dc.contributor.author | Vicario Hernando, José Luis | |
dc.date.accessioned | 2023-12-11T09:41:43Z | |
dc.date.available | 2023-12-11T09:41:43Z | |
dc.date.issued | 2018-03-12 | |
dc.identifier.citation | The Journal of Organic Chemistry 83(7) : 4180−4189(2018) | es_ES |
dc.identifier.issn | 0022-3263 | |
dc.identifier.issn | 1520-6904 | |
dc.identifier.uri | http://hdl.handle.net/10810/63341 | |
dc.description.abstract | A diastereodivergent approach to highly substituted bicyclo[3.1.0]hexanes has been developed through a transannular alkylation reaction that builds up the bicyclic core employing asymmetric organocatalysis as the tool for the installation of all stereocenters. On one hand, a Michael/Michael cascade process between enals and 4-alkenyl sulfamidate imines under the iminium/enamine activation manifold provides an oxathiazole-2,2-dioxide-fused cyclohexane adduct that, after isolation, is subsequently engaged in a transannular alkylation/hydrolysis through enamine activation by the use of a primary amine. On the other hand, the corresponding C-2 epimers are directly obtained from the same starting materials in a single operation through a cascade Michael/Michael/transannular alkylation/hydrolysis sequence through sequential iminium/enamine/enamine combination of aminocatalytic activation manifolds. | es_ES |
dc.description.sponsorship | Spanish MINECO (FEDER-CTQ2017-83633-P), Basque Government (IT908-16), UPV/EHU (EHUA15/24, EHUA16/10, and a fellowship to I.R.), COST Action CM1407 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/FEDER-CTQ2017-83633-P | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.title | Organocatalytic Transannular Approach to Stereodefined Bicyclo[3.1.0]hexanes | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2018, American Chemical Society | es_ES |
dc.relation.publisherversion | https://pubs.acs.org/doi/10.1021/acs.joc.8b00165 | es_ES |
dc.relation.publisherversion | https://doi.org/10.1021/acs.joc.8b00165 | es_ES |
dc.identifier.doi | 10.1021/acs.joc.8b00165 | |
dc.departamentoes | Química orgánica II | es_ES |
dc.departamentoeu | Kimika organikoa II | es_ES |