Optically pure fullerodendron formed by diastereoselective Diels-Alder reaction

The Diels-Alder reaction between C(60) and anthryl glycodendron, which has D- or L-gluconamides at the terminals, gave a new fullerene glycodendron conjugate. Interestingly, the diastereoselective cycloaddition reaction proceeded upon the treatment of C60 with the anthryl dendron 3. Furthermore, optical pure fullerodendrons (-)-4L and (+)-4D, which were confirmed by (1)H and (13)C NMR spectroscopy, FT-IR, MALDI-TOF mass spectroscopic analysis, were isolated from the mixture of diastereomers. And their absolute configurations were predicted by the use of CD spectra. (C) 2010 Elsevier Ltd. All rights reserved.