Carbon centered radicals adjacent to a chiral amine and generated by the addition of alkyl radicals to racemic or enantiomerically pure acrylates 1 react with tributyltin hydride in high yields and moderate to good diastereoselectivity. 1,2-Asymmetric induction depends on the nature of the groups at the stereogenic and the prochiral center and is remarkably sensitive to changes in the aryl-o-substituent.