Diastereoselective addition of nitro compounds to α,β-unsaturated γ-butyrolactones

Herein, we report our results on the diastereoselective addition of nitro compounds to α,β-unsaturated γ-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 α,β-unsaturated γ-butyrolactones 7 and 8 to the corresponding trisubstituted keto-γ-butyrolactones 24 and 25 via a tandem Michael-Nef protocol is also described.

Graphical abstractHerein, we report the results on the diastereoselective addition of nitro compounds to α,β-unsaturated γ-butyrolactones to afford vicinal trans di- and trisubstituted γ-butyrolactones 9-17 in good yields and diastereoisomeric ratios. A one-pot Michael addition-Nef reaction is described for the stereoselective preparation of ketolactones 24 and 25.Download full-size image