Enantioselective Access to 3-Azabicyclo[3.1.0]hexanes by (CpRhIII)-Rh-x Catalyzed C-H Activation and Cp*Ir-III Transfer Hydrogenation
Rigid saturated nitrogen-containing scaffolds such as 3-azabicyclo[3.1.0]hexanes are very important and frequently occurring motifs in biologically active compounds. We disclose a flexible two-step protocol for their efficient and selective access. A tailored CpRh-III catalyst promotes alkenyl C-H functionalization of N-enoxysuccinimides engaging in rare cis-cyclopropanation of range of primary amines, the dicarbonyl cis-cyclopropanes are efficiently and completely diastereoselectively cyclized by a CpRh-III acrolein to access disubstituted cis-cyclopropanes in high enantio- and diastereoselectivity. Subsequently, in the presence of a broad catalyst via an iterative aminative transfer hydrogen to an exquisite set of substituted 3-azabicyclo[3.1.0]hexanes.
WOS:000820235100001
2022-05-10
6209
6215
REVIEWED