Subsequent reactions (both radical and polar bond formations) at the C-terminus generally take place with near complete stereocontrol to "regenerate" the original stereocenter in a predictable way. The SRS approach has been applied in numerous contexts over the years, although its use in radical chemistry has seen only limited applications. Indeed, several examples of intramolecular radical C-C bond formation have been reported. Intermolecular C-C bond formations in this context are all reliant Giese-type additions to electron deficient olefins such as Inoue's acyltellurium studies. To our knowledge, the use of Seebach-type SRS in transition metalcatalyzed radical cross coupling has not been disclosed. Meanwhile, radical retrosynthesis has been demonstrated in a variety of contexts to achieve more intuitive, perhaps even "LEGO"-like modular approaches to synthesis. This Article discloses how the principle of SRS can be leveraged in the union of inexpensive isoserine-derived redox active esters (RAE) to serve as convenient "cassettes" for reliable and facile construction of chiral aminoalcohols via Nielectrocatalytic decarboxylative coupling. As documented herein, this reaction manifold is applicable in both the early and late stages of drug/agrochemical discovery due to its inherent modularity and robust scalability.