Diastereoselective lithium salt-assisted 1,3-dipolar cycloaddition of azomethine ylides to the fullerene C60

An efficient method for the diastereoselective synthesis of 5-substituted 3,4-fulleroproline esters based on the lithium salt-assisted cycloaddition of azomethine ylides has been developed. A series of the fulleroproline esters containing either electron donating or electron withdrawing substituents was prepared with high yields and diastereoselectivities provided by the S-trans-configuration of ylide generated in situ from the corresponding Schiff base in the presence of a lithium salt and base. This method provides easy preparation of 3,4-fulleroproline derivatives suitable for fullerene-based peptide synthesis.

Graphical abstractDownload full-size image