Individual ((f,t)A)- and (C-f,C-t)-Fullerene-Based Nickel(II) Glycinates: Protected Chiral Amino Acids Directly Linked to a Chiral pi-Electron System

摘要

Stereoselective electrosynthesis of the first individual ((f,t)A)- and (C-f,C- t)-1,4-fullerene derivatives with a non-inherently chiral functionalization pattern is described, as well as the first example of an optically pure protected primary amino acid directly linked to the fullerene through only the chiral alpha-aminoacid carbon atom. An application of an auxiliary chiral nickel-Schiff base moiety as derivatizing agent allowed separation of ((f,t)A)-and (C-f,C-t)-1,4-fullerene derivatives using an achiral stationary phase, a separation which has never been done before.