SYNTHESIS OF β-FLUOROAZIDES : A ROUTE TO PRIMARY β-FLUORO AMINES

Article abstract of DOI:10.1016/S0022-1139(00)83025-0

Two ways for the synthesis of β-fluoroazides are presented.The first one uses 1,2,2-trifluoro-2-chloro triethylamine (FAR) as a fluorinating reagent on the corresponding azidoalcohols.It is a smooth reaction at room temperature, but is not stereospecific ; it works well for phenyl substituted or primary α-carbon β-fluoroazides.The second route is the substitution of the azide group for bromine on an appropriate fluorobromide in phase transfer conditions.It is stereospecific (except for one case).It works well to give pure diastereoisomers of β-fluoroazides with pseudo primary (with deuterium) or secondary α-carbon atoms.