Outlined in this proposal are principles directed toward the development of catalytic enantioselective additions to achiral imines. A great deal of progress in the development of a wide range of different catalytic enantioselective reactions has been reported in the last two decades. A noted omission, until only very recently, has been the addition to achiral imines. Reactions of this type form a new C-C bond with generation of a stereogenic carbon center alpha to an imine. Presented herein is the development of two-point binding motifs for achiral imines which will allow the imine substrate to bind in an organized fashion to a well defined chiral bis(oxazoline) Lewis acid complex. These imine/catalyst substrates will be used in additions of silyl ketene acetals and inter- and intramolecular imino-ene reactions. The general principles learned from these reactions will allow for expansion to other pi-nucleophiles.
