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Individual ( f,t A)‐ and ( f,t C)‐Fullerene‐Based Nickel(II) Glycinates: Protected Chiral Amino Acids Directly Linked to a Chiral π‐Electron System
Author(s) -
Levitskiy Oleg A.,
Grishin Yuri K.,
Semivrazhskaya Olesya O.,
Ambartsumyan Asmik A.,
Kochetkov Konstantin A.,
Magdesieva Tatiana V.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609792
Subject(s) - fullerene , electrosynthesis , moiety , nickel , chemistry , chiral derivatizing agent , asymmetric carbon , stereoselectivity , stereochemistry , amino acid , enantiomer , chiral column chromatography , organic chemistry , catalysis , electrochemistry , optically active , biochemistry , electrode
Stereoselective electrosynthesis of the first individual ( f,t A)‐ and ( f,t C)‐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 α‐amino‐acid carbon atom. An application of an auxiliary chiral nickel‐Schiff base moiety as derivatizing agent allowed separation of ( f,t A)‐ and ( f,t C)‐1,4‐fullerene derivatives using an achiral stationary phase, a separation which has never been done before.