2026-04-21T08:58:03Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/105002025-05-28T00:05:23Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Gold-Catalyzed “Back-to-Front” Synthesis of 4-Silyloxyindoles Muñoz Torres, Miguel Ángel Suárez Pantiga, Samuel Sanz Díez, Roberto Química Química orgánica Chemistry Chemistry, Organic A series of pyrrol-yn-glycol derivatives were easily prepared from simple pyrroles through a three-step sequence involving hydroxyalkylation-alkynylation-O-silylation. Their reaction with IPrAuNTf2 triggers a C2-pyrrole attack onto the activated alkyne and subsequent highly selective 1,2-migration of the oxyalkyl group in the intermediate spirocycle. This approach enables the efficient synthesis of a wide selection of regioselectively functionalized 4-hydroxyindoles, which represent important yet challenging indole scaffolds, in high yields. We gratefully acknowledge Ministerio de Ciencia e Innovación(PID2020-115789GB-C21/AEI/10.13039/501100011033), and Junta de Castilla y León and FEDER (BU028P23) forfinancial support. M.A. M.-T. thanks Junta de Castilla y Leónand Fondo Social Europeo for a predoctoral contract. S.S.-P.thanks Ministerio de Ciencia e Innovación and “NextGener-ationEU”/PRTR EU for a Ramón y Cajal contract (RYC2021-031533-I). 2025-05-27T11:45:42Z 2025-05-27T11:45:42Z 2024-06 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 1523-7060 http://hdl.handle.net/10259/10500 10.1021/acs.orglett.4c01581 1523-7052 eng Organic Letters. 2024, V. 26, n. 23, p. 4969-4974 https://pubs.acs.org/doi/10.1021/acs.orglett.4c01581 Atribución 4.0 Internacional http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess application/pdf American Chemical Society