Chiral bisazafulleroids

A method for the synthesis of chiral bisazafulleroids with a C2 chiral auxiliary was developed based on the reaction of chiral 1,4-tert-alkoxy-2,3-bisazidobutanes with C60. The synthetic strategy involves the formation of bismesylates by the reaction of C2 chiral diols with MsCl and Et3N. An intermediate product was formed by the reaction of bismesylates with NaN3 and DMF/H2O in the presence of 15-crown-5. The chiral bisazafulleroids were produced by the reaction of the intermediate product with C60 and chlorobenzene.