might instead be achieved in two simple stages: biocatalytic C-H oxidation of inexpensive 10 followed by two sequential radical cross-couplings of the resulting acid and alcohol functional groups. Herein we present a proof of concept for this generalizable logic with scalable biocatalytic access to numerous hydroxylated piperidines followed by modular radical cross couplings. In this fashion, the synthesis of numerous high-value enantiopure piperidines can be dramatically simplified.