Site-Selective Modification of a Porpholactone—Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones

Ana F. R. Cerqueira, Gustautas Snarskis, Jonas Zurauskas, Samuel Guieu, Filipe A. Almeida Paz, Augusto C. Tomé
2020 Molecules  
The reaction of meso-tetrakis(pentafluorophenyl)porpholactone with azomethine ylides and nitrones affords pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones that display, respectively, isobacteriochlorin- and chlorin-type UV–Vis spectra. These reactions are site-selective, yielding, respectively, 17,18- or 12,13-dihydroporpholactones. The crystal and molecular features of pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones were unveiled from single-crystal X-ray diffraction studies.
doi:10.3390/molecules25112642 pmid:32517216 fatcat:s6nso2kvbrhjpjsokoaqd476xa