Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

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

Enantioselective C–H Functionalization–Addition Sequence Delivers Densely Substituted 3-Azabicyclo[3.1.0]hexanes
Julia Pedroni, Nicolai Cramer
An enantioselective C–H functionalization 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 nucleophiles in one-pot processes enabling the rapid and modular construction of heavily substituted pyrrolidines.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07024

DOI: 10.1021/jacs.7b07024

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