J. Org. Chem. 2021, 86 (19), 13289–13309
DOI: 10.1002/slct.202001243
Savych V.; Mykhalchuk V.; Melnychuk P.; Isakov A.; Savchuk T.; Timoshenko V.; Siry S.; Pavlenko S.; Kovalenko D.; Hryshchuk O.; Reznik V.; Chalyk B.; Yarmolchuk V.; Rusanov E.
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).