1807941-67-8Relevant articles and documents
Bicyclic Pyrrolidines for Medicinal Chemistry via [3 + 2]-Cycloaddition
Chalyk, Bohdan A.,Hryshchuk, Oleksandr V.,Isakov, Andrii O.,Kovalenko, Dmytro V.,Melnychuk, Pavlo V.,Mykhailiuk, Pavel K.,Mykhalchuk, Vladimir L.,Pavlenko, Sergiy O.,Reznik, Vitalii A.,Rusanov, Eduard B.,Savchuk, Taras,Savych, Vladimir I.,Siry, Sergiy A.,Timoshenko, Vadim M.,Yarmolchuk, Vladimir S.
, p. 13289 - 13309 (2021/09/13)
A general approach to bicyclic fused pyrrolidines via [3 + 2]-cycloaddition between nonstabilized azomethyne ylide and endocyclic electron-deficient alkenes was elaborated. Push-pull alkenes and CF3-alkenes did not react with the azomethyne ylide under the previously reported conditions, and we developed a superior protocol (LiF, 140 °C, no solvent). Among obtained products were medchem-relevant bicyclic sulfones, monofluoro-, difluoro-, and trifluoromethyl-substituted pyrrolidines. This approach not only allowed preparation of novel molecules but also significantly simplified synthesis of the existing ones (e.g., sofinicline).
