A new route to fullerene substituted phenylalanine derivatives?

Chemical Communications Pub Date: 2004-10-25 DOI: 10.1039/B411118D

Abstract

A series of fullerene substituted phenylalanine derivatives have been prepared by the condensation of 1,2-(4′-oxocyclohexano)fullerene with ester or Boc protected (4-amino)phenylalanine, H2NC6H4CH2CH(COR1)(NHCOR2) (where R1 = OMe, R2 = Me; R1 = OH, R2 = Me, OtBu). Conversion of the imine to the corresponding amine is achieved by di-acid catalyzed hydroboration. Reaction of the N-Ac amino ester with BBr3 led to the formation of the parent amino acid, while the Boc-protected derivative readily undergoes coupling with NH2–Gly–OEt. The reduction of the imine is not accompanied by hydroboration of the fullerene cage.

Graphical abstract: A new route to fullerene substituted phenylalanine derivatives
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