Asymmetric route to pyridines bearing a highly functionalized 2-alkyl substituent by aziridine ring-opening reactions

The reactivity of the pyridyl-substituted aziridine with different N-, S-, and O-nucleophiles is examined in order to understand the optimal conditions allowing for a selective ring-opening. It is shown that complete or prevalent regioelectivity can be obtained by using cerium trichloride heptahydrate as a catalyst and the N-substituent can be removed by an oxidative protocol.