Enantioselective C-H Functionalization-Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes

An enantioselective C-H functioffalization route to perfluoroalkyl-containing 3-azabicyclo[3.1.0]-hexanes is disclosed. A modular and bench-stable diazaphospholane ligand enables highly enantioselective Pd(0)-catalyzed cyclopropane C-H functionalization using trifluoroacetimidoyl chlorides as electrophilic partners. In turn, the resulting cyclic ketimine products react smoothly with a broad variety of nudeophiles in one-pot processes enabling the rapid and modular construction of heavily substituted pyrrolidines.