α,β-Unsaturated-δ-lactones are found in a number of biologically active natural products, such as fostriecin, leustroducsin, and pironetin. Traditional methods for the synthesis of the key scaffold involve hetero Diels-Alder and ring-closing metathesis among others. In our previous work, it was found that propiolic acids function as an equivalent of a 1,4-C,O-dipole for [4+2] annulation of α,β-unsaturated-δ-lactones. Here a mediocre enantioselectivity (upto 65 %ee obtained with DM-Segphos) indicates a challenge in asymmetric Au(I)-catalyzed intermolecular reaction. Enantio-discriminating step in this reaction presumably involves prochiral facial discrimination of the olefin nucleophile which is positioned away from the chiral ligand on gold. Our initial efforts to modify the chiral backbone of the ligand resulted on only poor enantioselectivity. However, change of solvent and counter-anion had profound effect on the enantioselectivity and we identified 1,1,2,2-tetrachloroethane and KB(C6F5)4 as the optimal combination of solvent and counter-anion. Although 80~98%ee was achieved under these conditions, some substrates still gave poor yields (20~50 %), presumably because of the side product resulting from the liberated isobutene. After extensive experiments, we found that addition of surfactants had beneficial effects on yields with some substrates giving higher enantioselectivity as well. Updates on the effect of amphiphile in terms of olefin substrate classes as well as the possible explanation for this effect will be discussed in this presentation.