Enantioselective Synthesis of Fluoroalkyl-Substituted <i>syn</i>-Diamines by the Asymmetric <i>gem</i>-Difunctionalization of 2,2,2-Trifluorodiazoethane
Jiuling Li, Dan Zhang, Jianghui Chen, Chaoqun Ma, Wenhao Hu
Abstract
We describe a facile strategy for building enantioenriched fluoroalkyl-substituted syn -diamines by the asymmetric gem -difunctionalization of 2,2,2-trifluorodiazoethane, which could be efficiently converted to a series of fluoroalkyl-substituted structures. The proposed key intermediate is an ammonium ylide generated from 2,2,2-trifluorodiazoethane, and its reactivity was further explored by DFT calculations.
Topics & Concepts
Enantioselective synthesisReactivity (psychology)YlideCatalysisChemistryCombinatorial chemistryAmmoniumOrganic chemistryMedicinePathologyAlternative medicineFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Reactions of Organic Compounds