Highly Diastereoselective [3 + 2] Cycloaddition of
Aziridines with Difluorinated Silyl Enol Ethers: Divergent Synthesis
of 4,4-Difluoropyrrolidines and 4‑Fluoropyrroles
posted on 2024-01-12, 14:36authored byHaijian Wu, Yanan Li, Manman Sun, Jing Zhang, Jinshan Li, Jianguo Yang
A highly
diastereoselective [3 + 2] cycloaddition of aziridines
with difluorinated silyl enol ethers has been developed. This approach
provides a facile methodology for highly functionalized gem-difluorinated pyrrolidines in good to excellent yields with good
functional group tolerance. A one-pot, two-step approach for synthesis
of structurally interesting fluorinated pyrroles has also been developed
through a cycloaddition/aromatization/desulfonation sequence. Moreover,
readily available substrates, mild reaction conditions, and easy scale-up
synthesis show practical advantages.