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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 287-291

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

Pier Giorgio Cozzi and Eleonora Rivalta

Alma Mater Studiorum, University of Bologna, Dipartimento di Chimica "G. Ciamician", Via Selmi 2, 40126 Bologna, Italy

Abstract: 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 Rh- and 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.