First enantioselective one-pot, three-component imino Reformatsky reaction*

The Reformatsky reaction is the well-recognized carbon–carbon bond-forming reaction of α-halo esters with aldehydes or ketones in the presence of Zn metal to give β-hydroxy esters. Recently, it has been reported that Rhand Ni-catalyzed Reformatsky reaction, in which R2Zn (R = Me, Et) acts as the Zn source, reacted smoothly with carbonyl compounds and imines. Taking advantage of N-methylephedrine as a cheap and recoverable chiral ligand, we have discovered the first homogeneous enantioselective Ni-catalyzed imino Reformatsky reaction. The process is a one-pot, three-component reaction, in which Me2Zn plays multiple roles as dehydrating agent, reductant, and coordinating metal. Broad scope, high enantiomeric excess, and a simple procedure are adding value to our findings.