Rhodium-Catalyzed\nEnantioselective Ring-Openings of\nOxabicyclic Alkenes with Azole Nucleophiles

We report enantioselective ring-openings of oxabicyclic\nalkenes\nwith azole nucleophiles, generating heterocycle-bearing dihydronaphthalene\nproducts. Pyrazoles, triazoles, tetrazoles, and benzo-fused derivatives\nparticipate in the ring-opening, with the level of regioselectivity\ndepending on the type and substitution pattern of the heterocyclic\npartner. Electron-withdrawing azole substituents have a beneficial\neffect, suppressing the unproductive complexation of a nitrogen with\nthe Rh(I)-bis(phosphine) catalyst.