Highly Diastereoselective [3 + 2] Cycloaddition of Aziridines with Difluorinated Silyl Enol Ethers: Divergent Synthesis of 4,4-Difluoropyrrolidines and 4-Fluoropyrroles
Haijian Wu, Yanan Li, Manman Sun, Jing Zhang, Jinshan Li, Jianguo Yang
Abstract
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.
Topics & Concepts
CycloadditionSilylationEnolAromatizationChemistryFunctional groupCombinatorial chemistryOrganic chemistryCatalysisPolymerFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions