148857-42-5Relevant articles and documents
Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-openingen routeto halohydrins
Ielo, Laura,Miele, Margherita,Pillari, Veronica,Senatore, Raffaele,Mirabile, Salvatore,Gitto, Rosaria,Holzer, Wolfgang,Alcántara, Andrés R.,Pace, Vittorio
supporting information, p. 2038 - 2043 (2021/03/16)
The intrinsic degradative α-elimination of Li carbenoids somehow complicates their use in synthesis as C1-synthons. Nevertheless, we herein report how boosting such an α-elimination is a straightforward strategy for accomplishing controlled ring-opening of epoxides to furnish the corresponding β-halohydrins. Crucial for the development of the method is the use of the eco-friendly solvent 2-MeTHF, which forces the degradation of the incipient monohalolithium, due to the very limited stabilizing effect of this solvent on the chemical integrity of the carbenoid. With this approach, high yields of the targeted compounds are consistently obtained under very high regiocontrol and, despite the basic nature of the reagents, no racemization of enantiopure materials is observed.
2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
supporting information; experimental part, p. 1380 - 1382 (2010/09/05)
An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.