Kinetic Resolution and Double Stereodifferentiation in Catalytic Asymmetric C−H Activation of 2-Substituted Pyrrolidines

Dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) (Rh(2)(S-DOSP)(4)) catalyzed decomposition of methyl aryldiazoacetates in the presence of 2-substituted pyrrolidines results in highly diastereoselective and enantioselective C-H insertions. These reactions can proceed with impressive levels of double stereodifferentiation and kinetic resolution, which allows for three stereocenters to be controlled during the C-H insertion step.