From the standpoint of logic employed in a medicinal chemistry setting this method offers increased convergency and modularity that is, in principle, amenable to parallel library synthesis. In terms of scalability, the reaction is easily conducted on a gram-scale as exemplified with the preparation of compound 28 without significant loss of reaction efficiency (Figure ). To further demonstrate the synthetic utility of this method, chiral a-amino ketone 6 was smoothly reduced to anti-1,2-amino alcohol 68 in a highly stereoselective fashion. The benzoyl group of 68 could be readily removed under mild conditions and swapped to Boc group with no erosion of enantiopurity (Figure ). In addition, the optimal conditions outlined herein provide promising preliminary results for the coupling of acid chloride 66 and other types of substrates 70 and 72 (Figure ). It is anticipated that further optimization of these substrate classes through ligand screening would lead to general methods. In terms of the mechanism of this transformation, it is likely following a similar pathway to other Ni-catalyzed reductive cross coupling reactions studied previously. To conclude, this study delineates a useful and practical approach to the synthesis of enantioenriched a-amino/amido ketones using Ni-catalysis. Predicated on a radical retrosynthetic strategy, it dramatically simplifies the routes to such structures allowing for convergent assembly of two carboxylates, one of which is a simple acyl chloride and one of which is an a-amido-containing RAE. The chemoselectivity of the reaction is high and as such the substrate scope is broad. The documented ability of this method to render access to known structures using only a fraction of the effort previously required bodes well for its widespread adoption.