It is anticipated that the platform described in this study for accessing substituted aminoalcohols will be useful in many different contexts, both academic and industrial. A simple, serine-derived cassette (10-RAE) was developed and tested across an array of useful C-C bond forming radical cross coupling reactions (both electrochemical and chemical) with broad scope (60 examples) as a consequence of the enhanced chemoselectivity of such transforms. Its unassailable utility was demonstrated through the simplified synthesis of 15 different building blocks and natural products that have been made before using conventional polar bond analysis. Finally, the scalability of electrocatalytic decarboxylative arylation of such systems was field-tested thereby verifying that such chemistry is suitable for both small and large scale applications. This work is yet another chapter in the evolving story of how radical retrosynthesis can contribute to streamlining the way organic molecules can be made.