[60]Fullerene l -Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior

2017

International audience; A new method to link amino acid and peptide derivatives to [60]fullerene is described. It uses hydrophosphination with a secondary phosphine borane. First, the stereoselective synthesis of secondary phosphine borane amino acid derivatives was achieved by alkylation of phenylphosphine borane with gamma-iodo-alpha-amino ester reagents under phase transfer catalysis (PTC). Second, a sec-phosphine borane amino ester was saponified and coupled with alpha,gamma-diamino esters to afford the corresponding dipeptide derivatives in good yields. Finally, the hydrophosphination reaction of [60]fullerene by the sec-phosphine borane compounds was performed under PTC to obtain C-60…