Conjugate addition of L-Selectride to α, β-enoyl sultams 1 and 4 followed by electrophilic trapping of the resulting enolates gave in one operation saturated imides with high β- and/or α- stereodifferentiation. Starting from enoylsultams, 1,4-reduction with L-Selectride followed by protonation or methylation gave α- and/or β-substituted imides with high asymmetric induction at both centers.