RT Journal Article
T1 Rare Gold-Catalyzed 4-exo-dig Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (Z)‑Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines
A1 Salvadó, Oriol
A1 Pérez Ruíz, Jorge
A1 Mesas, Alba
A1 Díaz Requejo, María Mar
A1 Pérez Romero, Pedro José
A1 Fernández Gutiérrez, Elena
AB We report an uncommon 4-exo-dig cyclization of N-tosyl homopropargyl amines, catalyzed by [AuCl(PEt3)]/AgOTf, to prepare stereoselective (Z)-2-alkylidene-1-tosylazetidine compounds. The reaction outcome contrasts with the gold-catalyzed cyclization of N-tosyl homopropargyl amines containing a methyl group at the propargylic position that provides substituted 2,3-dihydropyrroles via a 5-endo-dig mechanism. The access to N-tosyl homopropargyl amines is possible by the regioselective nucleophilic attack of α-diboryl alkylidene lithium salts to propargylic aziridines
PB American Chemical Society
SN 1523-7060
SN 1523-7052 (electrónico)
YR 2024
FD 2024-09
LK https://hdl.handle.net/10272/24247
UL https://hdl.handle.net/10272/24247
LA eng
NO Salvadó, O., Pérez-Ruíz, J., Mesas, A., Díaz-Requejo, M. M., Pérez, P. J., & Fernández, E. (2024). Rare Gold-Catalyzed 4-exo-dig Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (Z)-Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines. In Organic Letters (Vol. 26, Issue 36, pp. 7535–7540). American Chemical Society (ACS). https://doi.org/10.1021/acs.orglett.4c02415
NO The authors thank Ministerio de Economía y Competitividadand Fondo Europeo de Desarrollo Regional (FEDER) throughProjects PID2022-141693NB-I00, PID2020-113797RB-C21,and RED2022-134074-T, founded by MCIN/AEI/10.13039/501100011033 and “ERDF-A Way of Making Europe”
DS Repositorio Institucional de la Universidad de Huelva
RD 29 may 2026