Desymmetrization of cyclic meso-epoxides with silicon tetrachloride catalyzed by PINDOX, a chiral bipyridine mono-N-oxide.

PINDOX 8 has been identified as a chiral organocatalyst for the enantioselective ring-opening of cyclic meso-epoxides with SiCl(4) to produce chlorohydrins in up to 90% ee. The catalyst is most effective with saturated cyclic substrates containing more than seven carbon units.