The asymmetric allylation and crotylation of aromatic aldehydes with allylic trichlorosilanes catalyzed by substoichiometric quantities of chiral phosphoramides were carried out with good enantiomeric excess (up to 88% ee). Phosphoramides 3 and 4, prepared from (S)-proline, gave chiral homoallylic alcohols 6 and their enantiomers 7, respectively, with similar levels of enantioselectivity.