The first highly enantioselective synthesis of difluorinated azabicyclo[3.1.0] hexanes using an asymmetric Cu(I)-catalyzed (3+2) cycloaddition of azomethine ylides and fluorinated cyclopropenes. A focused library of 20 of these biosisosteric scaffolds has been synthesized with excellent yields of up to 97%, excellent diastereoselectvities of greater than 20:1 exo/endo selectivity and enantioselectivities of up to 98% ee. Furthermore, the utility of this reaction through its amenability to scale up and late-stage functionalization. Difluorinated azabicyclo[3.1.0] hexanes can be used as molecular building blocks through further functionalization that showcases their potential use in medicinally relevant molecules. Additionally, based on the unique chemical behaviour inherent to difluorinated cyclopropenes in this reaction additional DFT calculations are required to understand the mechanism.