Pyridine stabilized oxiranyl remote anions

The chemistry of oxiranyl remote anions derived from α,β-epoxypyridines is investigated. Deprotonation of α,β-epoxy pyridines at the β-position and reactions of the corresponding anions with a variety of electrophiles are found to be highly regioselective, possibly as a consequence of stabilization from the chelation between lithium and the pyridine moiety in the form of a five-membered cyclic intermediate.