Asymmetric epoxidation catalyzed by d-glucose-derived uloses

Three ulose catalysts () were prepared from d-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose and in asymmetric epoxidation was poor (up to 26% ee). Ulose afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (−)-trans-stilbene oxide.