A catalytic enantioselective imino-reformatsky reaction

The admission of air in the reaction mixture of imine, ethyl iodoacetate and dimethylzinc, in the presence of 20-30 mol % of inexpensive and commercially available N-methylephedrine as the chiral ligand, promoted the Reformatsky reaction, without the need for other metals or catalysts. Excellent yields (up to 92 %) and enantioselectivities (83-94 %) were obtained for the tested substrates. The reaction shows a broad scope, and all the imines are prepared in situ, using Me2Zn as the dehydrating agent.