Garre et al. Org Biomol Chem. 2023;21(13):2705-2708. Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.

Publicaciones > Garre et al

Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.

1. Universidad de Alcalá (IRYCIS), Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Campus Científico-Tecnológico, Facultad de Farmacia, Autovía A-II, Km 33.1, 28805-Alcalá de Henares, Madrid, Spain.  2. Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain.

ajuanjose.vaquero@uah.es  bjuanjose.vaquero@uah.es  cjuanjose.vaquero@uah.es  djuanjose.vaquero@uah.es  ejuanjose.vaquero@uah.es  fjuanjose.vaquero@uah.es  gjuanjose.vaquero@uah.es

Abstract

Cyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cyclization of related alcohols and acids, is supported by DFT calculations.

graphical abstract