The First Highly Enantioselective Lewis Base Organocatalyzed Hydrosilylation of α-Imino Esters

Novel, chiral Lewis base organocatalysts, which displayed poor enantioselection in the hydrosilylation of N-aryl beta-enamino esters, were found to be the catalysts of choice in the hydrosilylation of alpha-imino esters. In the presence of 10 mol-% of the best catalyst, various alpha-imino esters underwent enantioselective hydrosilylation to provide a wide range of chiral alpha-amino esters with good yields (up to 97%) and high enantioselectivities (up to 93% ee) except for some special substrates.