@article{10272/24247,
year = {2024},
month = {9},
url = {https://hdl.handle.net/10272/24247},
abstract = {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},
organization = {The authors thank Ministerio de Economía y Competitividad
and Fondo Europeo de Desarrollo Regional (FEDER) through
Projects PID2022-141693NB-I00, PID2020-113797RB-C21,
and RED2022-134074-T, founded by MCIN/AEI/10.13039/
501100011033 and “ERDF-A Way of Making Europe”},
publisher = {American Chemical Society},
title = {Rare Gold-Catalyzed 4-exo-dig Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (Z)‑Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines},
doi = {10.1021/acs.orglett.4c02415},
author = {Salvadó, Oriol and Pérez Ruíz, Jorge and Mesas, Alba and Díaz Requejo, María Mar and Pérez Romero, Pedro José and Fernández Gutiérrez, Elena},
}