Journal
CHIRALITY
Volume 30, Issue 4, Pages 498-508Publisher
WILEY
DOI: 10.1002/chir.22815
Keywords
amino acids; axial chirality; chiral HPLC; kinetic of racemization; rotational energy barriers
Funding
- IKERBASQUE, Basque Foundation for Science
- Changzhou Jin-Feng-Huang program
- National Natural Science Foundation of China [21472082]
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Herein we present design, synthesis, chiral HPLC resolution, and kinetics of racemization of axially chiral Ni(II) complexes of glycine and di-(benzyl)glycine Schiff bases. We found that while the ortho-fluoro derivatives are configurationally unstable, the pure enantiomers of corresponding axially chiral ortho-chloro-containing complexes can be isolated by preparative HPLC and show exceptional configurational stability (t(1/2) from 4 to 216 centuries) at ambient conditions. Synthetic implications of this discovery for the development of new generation of axially chiral auxiliaries, useful for general asymmetric synthesis of -amino acids, are discussed.
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