In this study, modular and stereocontrolled access to variety of substituted chiral aminoalcohols was developed by leveraging the power of Ni-electrocatalytic decarboxylative coupling. A simple, isoserine-derived oxazolidine was identified as a useful template to enable highly diastereoselective installation of an aminoacohol unit. The high stereochemical fidelity is based on Seebach's SRS principle, which is an underutilized strategy in the context of stereocontrolled radical cross coupling. The reaction allow for the coupling of a variety of (hetero)aryl halides and tolerates functional groups that are problematic for cross-coupling in general such as free phenols and anilines. The reaction is robust and scalable, which is evident in the success of gram-scale couplings for compound 30 and 44. In addition, omission of Ag additive on scale further improves the practicality and reduces heterogeneity of reaction conditions. The utility of the reaction is illustrated in syntheses of 7 useful intermediates or drugs, 4 of which are highly important drugs