The stereoretentive nature of this process was next explored in the context of achieving diastereocontrol. It is well precedented in the literature that radical cross-coupling resets the stereochemistry of the reaction center with the resulting stereochemical outcome being dictated by preexisting stereocenters. Towards this end, racemic piperidone 52 was reduced (NaBH4) to afford alcohol 53 in a 3:1 trans/cis-mixture. The cis-isomer 53a was converted to the corresponding trans-sulfonylhydrazide 54a and after coupling with 12 afforded the trans-configured piperidine 55a with 20:1 selectivity. Not surprisingly, the cis-configured iodide 56b, prepared from transalcohol 53b, delivered trans-55a as the major product under conventional electrocatalytic radical cross-coupling conditions in three different solvents. In contrast, the trans-alcohol 53b could be converted into cis-sulfonylhydrazide 54b which retained the cis-configuration thereby affording cis-55b as the major product (5:1 d.r., easily separated by silica gel chromatography). Similarly, 3-hydroxy proline-derived cisand trans-sulfonylhydrazides 57, respectively, could be coupled in a stereoretentive fashion with 12 to afford a high-degree of stereoretention in adducts 58-cis (1:5.5, trans:cis) and 58-trans (15.6:1, trans:cis). Not surprisingly, "classic" electrocatalytic radical cross coupling conditions with 12 using either cis or trans iodide 59 furnished trans adduct 58 as the major product (8.1-8.2:1, trans:cis).