Herein, we report our results on the diastereoselective addition of nitro compounds to alpha,beta-unsaturated gamma-butyrolactones, which afforded the corresponding Michael adducts 9-17 in moderate to good yields and good to excellent diastereoisomeric ratio. A one-pot conversion of alpha,beta-unsaturated gamma-butyrolactones 7 and 8 to the corresponding trisubstituted keto-gamma-butyrolactones 24 and 25 via a tandem Michael-Nef protocol is also described. (c) 2005 Elsevier Ltd. All rights reserved.472185188