A metal-free, mild, one-pot procedure has been developed to synthesize a number of homoallylic amines via a direct alkylative reductive amination of anilines and benzaldehydes using 1-allylsilatrane. The resulting homoallylic amines can been used to access various heterocycles ranging in size from 4, 5, and 6-membered rings. This method does not require the exclusion of water or air and tolerates a wide range of aromatic aldehyde and aniline substrates. We are currently investigating the expansion of this direct alkylative reductive amination reaction as applied to both ketones and aliphatic amines.