Catalytic Asymmetric One-Pot Aminofluorination of Enals

Significance

The authors present an amination-fluorination cascade reaction of aliphatic enals. In the presence of prolinol silylether 1, Cbz-protected methoxyamine was found to be a suitable amine nucleophile for the 1,4-addition to the substrates. Later on the 1-derived enamine of the amination product could be further reacted with an electrophilic fluorine source to give, after reduction, the α-fluoro-β-amino alcohols in reasonable yields and good to excellent diastereoselectivities and enantioselectivities in a one-pot procedure.