Ring opening of aziridines by different fluorinating reagents: Three synthetic routes to α,β-fluoro amines with different stereochemical pathways
Abstract
The syntheses of α,β-fluoro amines from the reaction of secondary aziridines with either Olah's reagent (HF, pyridine) or anhydrous hydrogen fluoride and of N-activated aziridines with partially neutralized Olah's reagent (NR3-nHF) are reported. The stereochemistry of these reactions is highly dependent on the structure of the starting compound and on the fluorinating agent. From the same aziridine it is thus possible to synthesize selectively each diastereoisomeric fluoro amine by proper choice of fluorination conditions. © 1981 American Chemical Society.