The synthesis of asymmetric 2-indolyl-4-methylenepiperidines 8-11 and 14-15 by condensation of an aminoallylsilane with an indole carbaldehyde, followed by intramolecular cyclization of the intermediate, is described. The reactivity of N-(2-hydroxyethyl)indolylpiperidines 9 and 14 with K t BuO to give indolo[2,3-α]quinolizidines is studied. Some unexpected results are obtained due to the influence of the α-phenyl ring.