Vicinal aminoalcohols are ubiquitous structural motifs present in many biologically active molecules as well as building blocks for organic synthesis (Figure ). In fact, more than one million compounds that are unsubstituted at C-1 and bear C-2 substitution can be found in Reaxys, including 88 approved drugs and >3600 natural products (for example compounds 1-7). As building blocks for organic synthesis, 2-substituted aminoethanols are a versatile input for chiral auxiliaries and catalysts. In medicinal chemistry they also serve as vital precursors for constructing chiral morpholines and piperazines. Numerous strategies to enantioselectively construct this unit have been reported over the years such as addition of nucleophilic carbon fragments into Garner's aldehyde, reduction of amino acids, asymmetric reductive amination and Sharpless asymmetric aminohydroxylation, all of which are accessed by polar bond analysis (2e - disconnections, Figure ). Although these approaches are valuable, a heavy reliance on harsh reactants such as organolithium/magnesium and LiAlH4 or toxic metals (Os) limits their widespread use. By far, the most widely adopted approach employs nucleophilic addition of organometallic reagents to chiral imines (Davis, Ellman, etc.). This strategy is modular and practical to conduct with the only caveat being a lack of chemoselectivity requiring additional protecting group manipulations with exposed acidic functional groups. Emblematic of this predicament is the reported enantiocontrolled synthesis of the natural product DAHD (3) through an 8-step route commencing from Garner's aldehyde wherein only 3 steps forge a C-C bond or install a key stereocenter. Attempts to add radicals to such imines have been met with limited success and require an additional electron withdrawing group or extended conjugation to enhance reactivity. Application of radical retrosynthetic logic to this problem could dramatically simplify access to such structures as has been demonstrated in a variety of different contexts. As transformations that proceed by way of radical intermediates are often compatible with common functional groups such as carbonyls and unprotected acidic/basic functionalities, the chemoselectivity issues present in polar bond disconnections might therefore disappear. However, the realization of this plan was elusive due to the lack of a suitable radical acceptor and reliable stereocontrol. Recently, we disclosed a Ni-electrocatlaytic decarboxylative coupling to access 1,2amino alcohols bearing substitution at the oxygen-bearing carbon leading to unbranched primary amino alcohols. Applying the same strategy using Seebach-type chiral redox active ester (RAE) mixture of diastereomers. Herein we disclose a simple and inexpensive solution to access this wide swath of chemical space utilizing an inexpensive, serine derived aminoalcohol cassette 10-RAE that serves to shield the polar aminoalcohol and uniformly control the stereochemistry of ensuing radical cross coupling reactions (Figure ). The scope of accessible stereopure 1,2aminoalcohols is vast due to the high chemoselectivity, thereby enabling dramatic synthetic simplification such as access to DAHD 3 in a single operation from 10-RAE.