We report the novel synthesis of various highly functionalized 3-arylaminomethyl indoles. This synthetic approach makes use of the directing ability of a bulky tert-butyldimethylsilyl-protecting group, which directs the condensation of an array of aromatic tosylaldimines specifically into the 3-position of the indole nucleus. The reactions, which occur under relatively mild conditions, afford the desired products in moderate yields. Prior to selective cleavage of the protecting group, the functionalized protected indoles also serve as attractive substrates for many future organic transformations.