A novel stereoselective route to γ-butyrolactones

Article abstract of DOI:10.1016/S0040-4039(00)91589-2

Treatment of the products obtained from conjugate additions of sulfoxides to α,β-unsaturated carbonyl compounds with soft electrophiles resulted in intramolecular displacement of the sulfinyl group by the carbonyl to give γ-butyrolactones. This novel cyclisation works best for benzylic sulfoxides and provides a concise route to trans-β,γ-disubstituted lactones with high stereoselectivity.