Herein, we report our results on the diastereoselective addition of nitro compounds to α, β- unsaturated γ-butyrolactones, which afforded the corresponding Michael adducts in moderate to good yields and good to excellent diastereoisomeric ratio. A one-pot conversion of α, β-unsaturated γ-butyrolactones and to the corresponding trisubstituted keto-γ- butyrolactones and via a tandem Michael–Nef protocol is also described.