Abstract The 1, 3-dipolar cycloaddition reactions of 2-diazocyclohexane-1, 3-dione (7a; Table 1) and of alkyl diazopyruvates (11a–e; Table 3) to 2, 3-dihydrofuran and other enol ethers have been investigated in the presence of chiral transition metal catalysts. With Rh II catalysts, the cycloadditions were not enantioselective, but those catalyzed by [Ru II Cl 2 (1a)] and [Ru II Cl 2 (1b)] proceeded with enantioselectivities of up to 58% and 74% ee, ...