The unique chemical and physical properties of fullerenes and their derivatives is mainly the result of their unique electron accepting abilities and their high charge transport capabilities in three dimensions. The octahedral arrangement of the addends in hexaadducts of C₆₀ is unique in organic chemistry. However, stereo-chemically controlled functionalization of fullerenes has been scarcely addressed so far. Here we report the synthesis and characterization of unprecedented D_2h-symmetrical trans-1-(S,R,R,S-bis-pyrrolidine)-tetra-malonate hexakis adducts of C₆₀, employing the topologically controlled method introduced by Krӓutler et al., followed by a 1,3-dipolar cycloaddition reaction.

Figure 1. Synthesis of D_2h-symmetrical trans-1-(S,R,R,S-bis-pyrrolidine)-tetra-malonate hexakis adducts of C₆₀.