Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines. -An amine-HF reagent is generated in situ from Bz-F/(CF3)2CH-OH and applied to a regio-and diastereoselective ring-opening of aziridine substrates. Medicinally important β-fluoroamine building blocks are produced with generally good to excellent yield. -(KALOW, J. A.; SCHMITT, D. E.; DOYLE*, A. G.; J. Org. Chem. 77 (2012) 8, 4177-4183, http://dx.doi.org/10.1021/jo300433a ; Dep. Chem., Princeton Univ., Princeton, NJ 08540, USA; Eng.) -Jannicke 32-048